Phenanthrene derivative, and material for organic el element

ABSTRACT

A phenanthrene derivative is represented by a formula (1) below. In the formula (1), Ar 1  and Ar 2  each represent an aromatic hydrocarbon ring group having 6 to 18 carbon atoms for forming the ring. The aromatic hydrocarbon ring group contains none of anthracene skeleton, pyrene skeleton, aceanthrylene skeleton and naphthacene skeleton. R 1  represents a substituent, the number of which may be 0, 1 or more. R 1  may be bonded in any position of the phenanthrene skeleton. n and m each represent an integer of 1 to 3. k represents an integer of 0 to 8.

TECHNICAL FIELD

The present invention relates to a phenanthrene derivative and amaterial for organic EL devices.

BACKGROUND ART

Organic electroluminescence devices (organic EL devices), which includeorganic emitting layers between anodes and cathodes, are known to emitlight using exciton energy generated by recombination of holes andelectrons injected into the organic emitting layers.

Such an organic EL device is advantageous as a self-emitting device, andexpected to serve as an emitting device excellent in luminousefficiency, image quality, power saving and thin design.

For use of an emitting material in an organic EL device, a dopingmethod, according to which a dopant material is doped to a hostmaterial, has been known as a usable method.

In order to efficiently generate exciton from injected energy and toefficiently use exciton energy for light emission, the exciton energygenerated by the host is transferred to the dopant, so that light isemitted from the dopant.

For instance, fused aromatic compounds and the like having phenanthreneskeletons shown in Patent Documents 1 to 11 have been used as the hostor dopant.

However, while there has recently been an increasing demand for organicEL devices excellent in luminous efficiency, heat resistance andlifetime and free from pixel defects, no organic-EL-device material orno host material has been found capable of providing such excellentorganic EL devices.

In this respect, in order to enhance internal quantum efficiency andachieve high luminous efficiency, developments have been made on anemitting material (phosphorescent material) that emits light usingtriplet exciton. In recent years, there has been a report on aphosphorescent organic device.

Since the internal quantum efficiency can be enhanced up to 75% or more(up to approximately 100% in theory) by using such a phosphorescentmaterial, an organic EL device having high efficiency and consuming lesspower can be obtained.

However, although exhibiting much higher luminous efficiency,traditional phosphorescent organic EL devices have such a short lifetimeas to be practically inapplicable.

Patent Document 1: JP-A-2007-84485

Patent Document 2: JP-A-2006-151966

Patent Document 3: JP-A-2005-19219

Patent Document 4: JP-A-2005-8588

Patent Document 5: JP-A-2004-18510

Patent Document 6: WO2007/46658

Patent Document 7: JP-A-2003-142267

Patent Document 8: JP-A-2004-75567

Patent Document 9: WO2006/114966

Patent Document 10: JP-A-2005-197262

Patent Document 11: WO2006/39982

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

In order to solve the above-described problems, an aspect of theinvention provides a phenanthrene derivative and organic-EL-devicematerial capable of providing an organic EL device excellent in luminousefficiency, heat resistance and lifetime and free from pixel defects.

Means for Solving the Problems

After conducting concentrated studies in order to achieve such anobject, the inventors have found that an organic EL device having highefficiency, high heat resistance and long lifetime without pixel defectscan be provided by using a phenanthrene derivative represented by thefollowing formula (1) as an organic-EL-device material, and reached thepresent invention.

A phenanthrene derivative according to an aspect of the invention isrepresented by a formula (1) below.

In the formula (1), Ar¹ and Ar² each represent an aromatic hydrocarbonring group having 6 to 18 carbon atoms for forming the ring, thearomatic hydrocarbon ring group containing none of anthracene skeleton,pyrene skeleton, aceanthrylene skeleton and naphthacene skeleton. Ar¹and Ar² may be bonded in any positions of the phenanthrene skeleton.

R¹ represents an alkyl group, cycloalkyl group, alkoxy group, cyanogroup, silyl group, halogen atom or an aryl group. R¹ may be bonded inany positions of the phenanthrene skeleton.

k represents an integer of 0 to 8, which represents the number ofsubstituents R¹ directly bonded to the phenanthrene main chain. When kis 2 or more, the plurality of R¹ may be mutually the same or different.

n and m each represent an integer of 1 to 3. When m+n≧2, the pluralitiesof Ar¹ and Ar² may be independently the same or different.

When (—[Ar¹]_(m)—H)=(—[Ar²]_(n)—H), at least either one of(—[Ar¹]_(m)—H) and (—[Ar²]—H) is bonded in 1st, 4th, 5th, 8th, 9th or10th position of the phenanthrene skeleton.

A material for organic EL devices according another aspect of theinvention contains the phenanthrene derivative represented by theformula (1).

An organic EL device according to a still further aspect of theinvention includes a single-layered or multilayered organic thin-filmlayer between a cathode and an anode, the organic thin-film layerincluding an emitting layer, at least one layer of the organic thin-filmlayer containing the phenanthrene derivative represented by the formula(1).

The aspects of the invention can provide a phenanthrene derivative andorganic-EL-device material capable of providing an organic EL deviceexcellent in luminous efficiency, heat resistance and lifetime and freefrom pixel defects.

BEST MODE FOR CARRYING OUT THE INVENTION

Exemplary preferable embodiment(s) of the invention will be describedbelow.

[Phenanthrene Derivative]

A phenanthrene derivative according to an aspect of the invention isrepresented by a formula (1) below.

In the formula (1), Ar¹ and Ar² each represent an aromatic hydrocarbonring group having 6 to 18 carbon atoms for forming the ring, thearomatic hydrocarbon ring group containing none of anthracene skeleton,pyrene skeleton, aceanthrylene skeleton and naphthacene skeleton. Ar¹and Ar² may be bonded in any positions of the phenanthrene skeleton.

R¹ represents an alkyl group, cycloalkyl group, alkoxy group, cyanogroup, silyl group, halogen atom or an aryl group. R¹ may be bonded inany position of the phenanthrene skeleton.

k represents an integer of 0 to 8, which represents the number ofsubstituents R¹ directly bonded to the phenanthrene main chain. When kis 2 or more, the plurality of R¹ may be mutually the same or different.

n and m each represent an integer of 1 to 3. When m+n≧2, the pluralitiesof Ar¹ and Ar² may be independently the same or different.

When m is 1 to 3, (—[Ar¹]_(m)—H) is represented by the following formula(1-m).

When m is 1, (—Ar^(1a)—H) is represented by the following formula(1-m-1).

When m is 2, (—Ar^(1a)—Ar^(1b)—H) is represented by the followingformula (1-m-2).

When m is 3, (—Ar^(1a)—Ar^(1b)—Ar^(1c)—H) is represented by thefollowing formula (1-m-3).

When n is 1 to 3, (—[Ar²]_(n)—H) is represented by the following formula(1-n).

When n is 1, (—Ar^(2a)—H) is represented by the following formula(1-n-1).

When n is 2, (—Ar^(2a)—Ar^(2b)—H) is represented by the followingformula (1-n-2).

When n is 3, (—Ar^(2a)—Ar^(2b)—Ar^(2c)—H) is represented by thefollowing formula (1-n-3).

Ar^(1a), Ar^(1b) and Ar^(1c) in the formulae (1-m-1) to (1-m-3) andAr^(1a), Ar^(2b) and Ar^(2c) in the formulae (1-n-1) to (1-n-3) may eachbe independently the same or different. When(—[Ar¹]_(m)—H)=(—[Ar²]_(n)—H), at least either one of (—[Ar¹]_(m)—H) and(—[Ar²]_(n)—H) is bonded in 1st, 4th, 5th, 8th, 9th or 10th position ofthe phenanthrene skeleton.

Herein, the “ring carbon atoms” means carbon atoms that form a saturatedring, unsaturated ring or aromatic ring, and the “ring atoms” meanscarbon atoms and hetero atoms that form a hetero ring (encompassing asaturated ring, unsaturated ring and aromatic ring).

The phenanthrene derivative according to the aspect of the invention isfavorably usable as an organic-EL-device material capable of providingan organic EL device excellent in luminous efficiency, heat resistanceand lifetime and free from pixel defects.

Organic compounds having an anthracene skeleton, pyrene skeleton,aceanthrylene skeleton or naphthacene skeleton exhibit such smalltriplet energy that the obtained phosphorescent organic EL device wouldhardly provide efficient emission. Thus, it is unfavorable that Ar¹ andAr² have these structures.

In addition, when Ar¹ and Ar² have more than 18 ring carbon atoms, thetriplet energy is reduced. Hence, unfavorably, the obtainedphosphorescent organic EL device would hardly provide efficientemission.

When m and n are more than 4, the molecular weight is increased, and thedeposition would not be favorably performed. Accordingly, m and n arepreferably 1 to 4.

Groups of compounds having highly symmetric molecular structures arehighly apt to be crystallized, so that such groups of compounds wouldhardly maintain their amorphousness while being formed into films.

In contrast, for instance, by:

(1) introducing a twist in the molecule with use of a steric hindrancecaused by a hydrogen atom in the peri position of a molecule to whichAr¹ or Ar² is bonded (e.g., when Ar¹ or Ar² is bonded in α-position of anaphthalene skeleton or when Ar¹ or Ar² substitutes a phenanthreneskeleton in 1st, 4th, 5th, 8th, 9th or 10th position);(2) introducing a sterically-hindered substituent; or(3) asymmetrically forming the molecule,it is possible to prevent the crystallization of the compound and toobtain a highly amorphous film.

When (—[Ar¹]_(m)—H)=(—[Ar²]_(n)—H) in the following general formulae(1-a) and (1-b), the molecule is symmetric with no twist. Thus, such acompound would be highly apt to be crystallized, and would hardlymaintain their amorphousness while being formed into films. Accordingly,these structures are excluded according to the aspect of the invention.

As described above, according to the aspect of the invention, themolecular asymmetry and the presence of twist in the molecule cansynergistically prevent the crystallization of the compound in the filmsof the organic EL device, which is indispensable in solving theproblems.

Only the phenanthrene derivative that satisfies all of the aboverequirements is favorably usable as an organic-EL-device materialcapable of providing an organic EL device excellent in luminousefficiency, heat resistance and lifetime and free from pixel defects.

In the above formula (1), R¹ is preferably selected from an aryl grouphaving 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms,a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1to 20 carbon atoms, a cyano group, a silyl group having 3 to 30 carbonatoms and a halogen atom.

Examples of the aryl group having 6 to 30 carbon atoms include a phenylgroup, a 1-naphthyl group, a 2-naphthyl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a9-phenanthryl group, a 2-biphenylyl group, a 3-biphenylyl group, a4-biphenylyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group,a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-ylgroup, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, ap-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenylgroup, a 3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4′-methylbiphenylyl group, and a 4′-t-butyl-p-terphenyl-4-yl group.

Examples of the alkyl group having 1 to 30 carbon atoms include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

Examples of the cycloalkyl group having 3 to 30 carbon atoms include_(a) cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and a3,5-tetramethylcyclohexyl group, and a cyclohexyl group, a cyclooctylgroup, and a 3,5-tetramethylcyclohexyl group are preferred.

The alkoxy group having 1 to 20 carbon atoms is a group represented by—OY. Examples of Y include a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an s-butyl group, anisobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, ann-heptyl group, an n-octyl group, a hydroxymethyl group, a1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxyisobutyl group,a 1,2-dihydroxyethyl group, a 1,3-dihydroxyisopropyl group, a2,3-dihydroxy-t-butyl group, a 1,2,3-trihydroxypropyl group, achloromethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a2-chloroisobutyl group, a 1,2-dichloroethyl group, a1,3-dichloroisopropyl group, a 2,3-dichloro-t-butyl group, a1,2,3-trichloropropyl group, a bromomethyl group, a 1-bromoethyl group,a 2-bromoethyl group, a 2-bromoisobutyl group, a 1,2-dibromoethyl group,a 1,3-dibromoisopropyl group, a 2,3-dibromo-t-butyl group, a1,2,3-tribromopropyl group, an iodomethyl group, a 1-iodoethyl group, a2-iodoethyl group, a 2-iodoisobutyl group, a 1,2-diiodoethyl group, a1,3-diiodoisopropyl group, a 2,3-diiodo-t-butyl group, a1,2,3-triiodopropyl group, an aminomethyl group, a 1-aminoethyl group, a2-aminoethyl group, a 2-aminoisobutyl group, a 1,2-diaminoethyl group, a1,3-diaminoisopropyl group, a 2,3-diamino-t-butyl group, a1,2,3-triaminopropyl group, a cyanomethyl group, a 1-cyanoethyl group, a2-cyanoethyl group, a 2-cyanoisobutyl group, a 1,2-dicyanoethyl group, a1,3-dicyanoisopropyl group, a 2,3-dicyano-t-butyl group, a1,2,3-tricyanopropyl group, a nitromethyl group, a 1-nitroethyl group, a2-nitroethyl group, a 2-nitroisobutyl group, a 1,2-dinitroethyl group, a1,3-dinitroisopropyl group, a 2,3-dinitro-t-butyl group, and a1,2,3-trinitropropyl group.

The silyl group having 3 to 30 carbon atoms is preferably, for instance,an alkylsilyl group or an aralkylsilyl group having 3 to 20 carbonatoms. Examples thereof include a trimethylsilyl group, a triethylsilylgroup, a tributylsilyl group, a trioctylsilyl group, a triisobutylsilylgroup, a dimethylethylsilyl group, a dimethylisopropylsilyl group, adimethylpropylsilyl group, a dimethylbutylsilyl group, adimethyltertiarybutylsilyl group, a diethylisopropylsilyl group, aphenyldimethylsilyl group, a diphenylmethylsilyl group, adiphenyltertiarybutyl group, and a triphenylsilyl group.

Examples of the halogen atom represented by R¹ include fluorine,chlorine, bromine, and iodine.

In the formula (1), the substituting position of Ar¹ and Ar² in thephenanthrene skeleton may be 1,2-position, 1,3-position, 1,4-position,1,5-position, 1,6-position, 1,7-position, 1,8-position, 1,9-position,1,10-position, 2,3-position, 2,4-position, 2,5-position, 2,6-position,2,7-position, 2,8-position, 2,9-position, 2,10-position, 3,4-position,3,5-position, 3,6-position, 3,7-position, 3,8-position, 3,9-position,3,10-position, 4,5-position, 4,6-position, 4,7-position, 4,8-position,4,9-position, 4,10-position or 9,10-position. The substituting positionis preferably 2,7-position, 2,9-position, 2,10-position, 3,6-position,4,9-position, 4,10-position or 9,10-position. When(—[Ar¹]_(m)—H)≠(—[Ar²]_(n)—H), the phenanthrene derivative is morepreferably a phenanthrene derivative represented by the followingformula (1-a) to formula (1-l) (see, Chemical Formula 4). When(—[Ar¹]_(m)—H)=(—[Ar²]_(n)—H), the phenanthrene derivative is morepreferably a phenanthrene derivative represented by the followingformula (1-c) to formula (1-l) (see, Chemical Formula 5).

In the formula (1), Ar¹ and Ar² each preferably represent a groupselected from a substituted or unsubstituted benzene skeleton,naphthalene skeleton, fluorene skeleton, fluoranthene skeleton,triphenylene skeleton, chrysene skeleton, benzophenanthrene skeleton,dibenzophenanthrene skeleton, benzotriphenylene skeleton, piceneskeleton and benzo[b]fluoranthene skeleton.

By employing these structures for Ar¹ and Ar², the triplet energy gapcan be made sufficiently large. Thus, the phenanthrene derivative isfavorably usable as a phosphorescent host capable of transferring energyto the phosphorescent emitting material.

It should be noted that a “fluorescent host” and a “phosphorescent host”herein respectively mean a host combined with a fluorescent dopant and ahost combined with a phosphorescent dopant, and that a distinctionbetween the fluorescent host and phosphorescent host is notunambiguously derived only from a molecular structure of the host in alimited manner.

In other words, the fluorescent host herein means a material for forminga fluorescent-emitting layer containing a fluorescent dopant, and doesnot mean a host that is only usable as a host of a fluorescent material.

Likewise, the phosphorescent host herein means a material for forming aphosphorescent-emitting layer containing a phosphorescent dopant, anddoes not mean a host that is only usable as a host of a phosphorescentmaterial.

In the formula (1), k is preferably 0, 1 or 2.

When Ar¹ and Ar² in the formula (1) have substituent(s), thesubstituent(s) is preferably a group selected from an alkyl group having1 to 30 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms,alkoxy group having 1 to 20 carbon atoms, cyano group, silyl grouphaving 3 to 30 carbon atoms and halogen atom. Examples of the alkylgroup, cycloalkyl group, alkoxy group and silyl group as thesubstituent(s) for Ar¹ and Ar² are the same as enumerated with respectto R¹.

Examples of the phenanthrene derivative according to the aspect of theinvention are as follows.

[Organic-EL-Device Material]

A material for organic EL devices according another aspect of theinvention contains the phenanthrene derivative represented by theformula (1).

The material for organic EL devices according to the aspect of theinvention is preferably used as the host material of the emitting layer.

By using the organic-EL-device material containing the phenanthrenederivative represented by the formula (1) as the host material of theemitting layer, an emitting layer of high efficiency and long lifetimeis obtainable.

[Organic EL Device]

Next, an organic EL device according to a still further aspect of theinvention will be described below.

The organic EL device according to the aspect of the invention includesa single-layered or multilayered organic thin-film layer providedbetween a cathode and an anode, and the organic thin-film layer includesan emitting layer. At least one layer of the organic thin-film layercontains the organic-EL-device material according to the aspect of theinvention.

Structure examples of a multilayered organic EL device are structuresthat respectively include: an anode, hole transporting layer (holeinjecting layer), emitting layer and cathode; an anode, emitting layer,electron transporting layer (electron injecting layer) and cathode; ananode, hole transporting layer (hole injecting layer), emitting layer,electron transporting layer (electron injecting layer) and cathode; andan anode, hole transporting layer (hole injecting layer), emittinglayer, hole blocking layer, electron transporting layer (electroninjecting layer) and cathode.

The organic EL device 1 includes a transparent substrate 2, an anode 3,a cathode 4 and an organic thin-film layer 10 positioned between theanode 3 and the cathode 4.

The organic thin-film layer 10 includes a phosphorescent-emitting layer5 containing host and phosphorescent dopant. A layer such as a holeinjecting/transporting layer 6 may be provided between thephosphorescent-emitting layer 5 and the anode 3 while a layer such as anelectron injecting/transporting layer 7 may be provided between thephosphorescent-emitting layer 5 and the cathode 4.

In addition, an electron blocking layer may be provided to thephosphorescent-emitting layer 5 adjacently to the anode 3 while a holeblocking layer may be provided to the phosphorescent-emitting layer 5adjacently to the cathode 4.

With this arrangement, electrons and holes can be trapped in thephosphorescent-emitting layer 5, thereby enhancing probability ofexciton generation in the phosphorescent-emitting layer 5.

It should be noted that the “hole injecting/transporting layer” hereinmeans “at least either one of a hole injecting layer and a holetransporting layer” while the “electron injecting/transporting layer”herein means “at least either one of an electron injecting layer and anelectron transporting layer.”

In the organic EL device according to the aspect of the invention, theemitting layer preferably contains the organic-EL-device materialaccording to the aspect of the invention as the host material. Further,the emitting layer preferably contains the host material and aphosphorescent-emitting material, and the host material is preferablythe organic-EL-device material.

Examples of the phosphorescent-emitting material are metal complexesthat contain: a metal selected from Ir, Pt, Os, Au, Cu, Re and Ru; and aligand. The phosphorescent-emitting material is preferably a compoundcontaining a metal selected from iridium (Ir), osmium (Os) and platinum(Pt) because such a compound, which exhibits high phosphorescencequantum yield, can further enhance external quantum efficiency of theemitting device. The phosphorescent-emitting material is more preferablya metal complex such as an iridium complex, osmium complex or platinumcomplex, among which an iridium complex and platinum complex are morepreferable and ortho metalation of an iridium complex is the mostpreferable. Further preferable examples of the ortho metalation of themetal complex are iridium complexes and the like shown below.

In the organic EL device according to the aspect of the invention, theemitting layer contains the host material and thephosphorescent-emitting material, and the above iridium complex is usedas the phosphorescent-emitting material.

In the aspect of the invention, the maximum wavelength of the emissionby the phosphorescent-emitting material is preferably 520 nm to 700 nm,more preferably 590 nm to 700 nm.

By doping the phosphorescent-emitting material (phosphorescent dopant)having such an emission wavelength to the organic-EL-device materialaccording to the aspect of the invention so as to form the emittinglayer, the organic EL device can exhibit high efficiency.

The organic EL device according to the aspect of the invention mayinclude the hole transporting layer (or the hole injecting layer). Thehole transporting layer (or the hole injecting layer) may preferablycontain the organic-EL-device material according to the aspect of theinvention. Alternatively, when the organic EL device according to theaspect of the invention includes at least either one of the electrontransporting layer and the hole blocking layer, the at least either oneof the electron transporting layer and the hole blocking layer maypreferably contain the organic-EL-device material according to theaspect of the invention.

In the organic EL device according to the aspect of the invention, areduction-causing dopant may be preferably contained in an interfacialregion between the cathode and the organic thin-film layer.

With this arrangement, the organic EL device can emit light withenhanced luminance intensity and have a longer lifetime.

The reduction-causing dopant may be at least one compound selected froman alkali metal, alkali metal complex, alkali metal compound, alkaliearth metal, alkali earth metal complex, alkali earth metal compound,rare-earth metal, rare-earth metal complex, rare-earth metal compoundand the like.

Examples of the alkali metal are Na (work function: 2.36 eV), K (workfunction: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95eV) and the like, among which a substance having a work function of 2.9eV or less is particularly preferable. Among the above, thereduction-causing dopant is preferably K, Rb or Cs, more preferably Rbor Cs, the most preferably Cs.

Examples of the alkali earth metal are Ca (work function: 2.9 eV), Sr(work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV) and thelike, among which a substance having a work function of 2.9 eV or lessis particularly preferable.

Examples of the rare-earth metal are Sc, Y, Ce, Tb, Yb and the like,among which a substance having a work function of 2.9 eV or less isparticularly preferable.

Since the above preferable metals have particularly high reducibility,addition of a relatively small amount of the metals to an electroninjecting zone can enhance luminance intensity and lifetime of theorganic EL device.

Examples of the alkali metal compound include an alkali oxide such asLi₂O, Cs₂O and K₂O, and an alkali halide such as LiF, NaF, CsF and KF.LiF, Li₂O, and NaF are preferable.

Examples of the alkali earth metal compound include BaO, SrO, CaO andtheir mixture such as Ba_(x)Sr_(1-x)O (0<x<1) and Ba_(x)Ca_(1-x)O(0<x<1). BaO, SrO, and CaO are preferable.

Examples of the rare earth metal compound include YbF₃, ScF₃, SeO₃,Y₂O₃, Ce₂O₃, GdF₃ and TbF₃. YbF₃, ScF₃, and TbF₃ are preferable.

The alkali metal complex, alkali earth metal complex and rare earthmetal complex are not specifically limited as long as they contain atleast one metal ion of an alkali metal ion, an alkali earth metal ionand a rare earth metal ion. In addition, the ligand is preferablyquinolynol, benzoquinolynol, acridinol, phenanthridinol,hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole,hydroxydiarylthiadiazole, hydroxyphenylpyridine,hydroxyphenylbenzoimidazole, hydroxybenzotriazole, hydroxyfluboran,bipyridyl, phenanthroline, phthalocyanin, porphyrin, cyclopentadiene,β-diketones, azomethines, and derivatives thereof. However, the ligandis not limited thereto.

The reduction-causing dopant is added to preferably form a layer or anisland pattern in the interfacial region. The layer of thereduction-causing dopant or the island pattern of the reduction-causingdopant is preferably formed by depositing the reduction-causing dopantby resistance heating deposition while an emitting material for formingthe interfacial region or an organic substance as an electron-injectingmaterial are simultaneously deposited, so that the reduction-causingdopant is dispersed in the organic substance. Dispersion concentrationat which the reduction-causing dopant is dispersed in the organicsubstance is a mole ratio (organic substance to reduction-causingdopant) of 100:1 to 1:100, preferably 5:1 to 1:5.

When the reduction-causing dopant forms the layer, the emitting materialor the electron injecting material for forming the organic layer of theinterfacial region is initially layered, and the reduction-causingdopant is subsequently deposited singularly thereon by resistanceheating deposition to form a preferably 0.1 to 15 nm-thick layer.

When the reduction-causing dopant forms the island pattern, the emittingmaterial or the electron injecting material for forming the organiclayer of the interfacial region is initially formed in an island shape,and the reduction-causing dopant is subsequently deposited singularlythereon by resistance heating deposition to form a preferably 0.05 to 1nm-thick island shape.

A ratio of the main component to the reduction-causing dopant in theorganic EL device according to the aspect of the invention is preferablya mole ratio (main component to reduction-causing dopant) of 5:1 to 1:5,more preferably 2:1 to 1:2.

The organic EL device according to the aspect of the inventionpreferably includes the electron injecting layer between the emittinglayer and the cathode, and the electron injecting layer preferablycontains a nitrogen-containing cyclic derivative as the main component.

It should be noted that “as the main component” means that thenitrogen-containing cyclic derivative is contained in the electroninjecting layer at a content of 50 mass % or more.

The electron injecting layer or the electron transporting layer, whichaids injection of the electrons into the emitting layer, has a highelectron mobility. The electron injecting layer is provided foradjusting energy level, by which, for instance, sudden changes of theenergy level can be reduced.

A preferable example of an electron transporting material for formingthe electron injecting layer is an aromatic heterocyclic compound havingin the molecule at least one heteroatom. Particularly, anitrogen-containing cyclic derivative is preferable.

A preferable example of the nitrogen-containing cyclic derivative is anitrogen-containing cyclic metal chelate complex represented by thefollowing formula (A).

R² to R⁷ each independently represent a hydrogen atom, a halogen atom,an oxy group, an amino group, a hydrocarbon group having 1 to 40 carbonatoms, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, or aheterocyclic group. These groups may be substituted or unsubstituted.

Examples of the halogen atom include fluorine, chlorine, bromine, andiodine. In addition, examples of the substituted or unsubstituted aminogroup include an alkylamino group, an arylamino group, and anaralkylamino group.

Examples of the hydrocarbon group having 1 to 40 carbon atoms include asubstituted or unsubstituted alkyl group, an alkenyl group, a cycloalkylgroup, an aryl group, and an aralkyl group.

Examples of the alkyl group include a methyl group, an ethyl group, apropyl group, an isopropyl group, an n-butyl group, an s-butyl group, anisobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, ann-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, ann-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, a neopentyl group, a1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a1-butylpentyl group, a 1-heptyloctyl group, a 3-methylpentyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 1,2-dinitroethylgroup, a 2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

Among these, preferred are a methyl group, an ethyl group, a propylgroup, an isopropyl group, an n-butyl group, an s-butyl group, anisobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, ann-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, ann-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, a neopentyl group, a1-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, anda 1-heptyloctyl group.

Examples of the alkenyl group include a vinyl group, an allyl group, a1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1,3-butanedienyl group, a 1-methylvinyl group, a styryl group, a2,2-diphenylvinyl group, a 1,2-diphenylvinyl group, a 1-methylallylgroup, a 1,1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallylgroup, a 2-phenylallyl group, a 3-phenylallyl group, a 3,3-diphenylallylgroup, a 1,2-dimethylallyl group, a 1-phenyl-1-butenyl group, and a3-phenyl-1-butenyl group. A styryl group, a 2,2-diphenylvinyl group, anda 1,2-diphenylvinyl group are preferred.

Examples of the cycloalkyl group include a cyclopentyl group, acyclohexyl group, a cyclooctyl group, and a 3,5-tetramethylcyclohexylgroup. A cyclohexyl group, a cyclooctyl group, and a3,5-tetramethylcyclohexyl group are preferable.

The alkoxy group is a group represented by —OY. Example of Y are thesame as those described above for the alkyl group. The preferredexamples are also the same.

Examples of the non-fused aryl group include a phenyl group, abiphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, ap-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a4′-methylbiphenylyl group, a 4″-t-butyl-p-terphenyl-4-yl group, ano-cumenyl group, an m-cumenyl group, a p-cumenyl group, a 2,3-xylylgroup, a 3,4-xylyl group, a 2,5-xylyl group, a mesityl group, and anm-quarterphenyl group.

Among these, preferred are a phenyl group, a biphenyl-2-yl group, abiphenyl-3-yl group, a biphenyl-4-yl group, an m-terphenyl-4-yl group,an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, a p-tolyl group, a3,4-xylyl group, and an m-quarterphenyl-2-yl group.

Examples of the fused aryl group include a 1-naphthyl group and a2-naphthyl group.

The heterocyclic group is a mono ring or a fused ring. The heterocyclicgroup preferably has 1 to 20 ring carbon atoms, more preferably 1 to 12ring carbon atoms, and still more preferably 2 to 10 ring carbon atoms.An example thereof is an aromatic heterocyclic group having at least onehetero atom selected from a nitrogen atom, an oxygen atom, a sulfur atomand a selenium atom. Examples of the heterocyclic group include groupsthat are derived from pyrrolidine, piperidine, piperazine, morpholine,thiophene, selenophene, furan, pyrrol, imidazole, pyrazole, pyridine,pyrazine, pyridazine, pyrimidine, trizaole, triazine, indole, indazole,purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole,oxadiazole, quinoline, isoquinoline, phthalazine, naphthridine,quinoxaline, quinazoline, cinnoline, pteridine, acridine,phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole,benzothiazole, benzotriazole, tetrazaindene, carbazole, and azepine.Preferably, the heterocyclic group is derived from furan, thiophene,pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline,phthalazine, naphthiridine, quinoxaline and quinazoline. Morepreferably, the heterocyclic group is a group derived from furan,thiophene, pyridine and quinoline, and still more preferably aquinolinyl group.

Examples of the aralkyl group include a benzyl group, a 1-phenylethylgroup, a 2-phenylethyl group, a 1-phenylisopropyl group, a2-phenylisopropyl group, a phenyl-t-butyl group, a α-naphthylmethylgroup, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, ap-methylbenzyl group, an m-methylbenzyl group, an o-methylbenzyl group,a p-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzylgroup, a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzylgroup, a p-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzylgroup, a p-hydroxybenzyl group, an m-hydroxybenzyl group, ano-hydroxybenzyl group, a p-aminobenzyl group, an m-aminobenzyl group, ano-aminobenzyl group, a p-nitrobenzyl group, an m-nitrobenzyl group, ano-nitrobenzyl group, a p-cyanobenzyl group, an m-cyanobenzyl group, ano-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group.

Among these, preferred are a benzyl group, a p-cyanobenzyl group, anm-cyanobenzyl group, an o-cyanobenzyl group, a 1-phenylethyl group, a2-phenylethyl group, a 1-phenylisopropyl group, and a 2-phenylisopropylgroup.

The aryloxy group is represented by —OY′. Examples of Y′ include aphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group,a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4% methylbiphenylyl group, and a4′-t-butyl-p-terphenyl-4-yl group.

The heteroaryloxy group in the aryloxy group is represented by —OZ′.Examples of Z′ include a 2-pyrrolyl group, a 3-pyrrolyl group, apyrazinyl group, a 2-pyrizinyl group, a 3-pyrizinyl group, a 4-pyrizinylgroup, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a5-indolyl group, a 6-indolyl group, a 7-indolyl group, a 1-isoindolylgroup, a 3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group,a 6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolylgroup, a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a7-quinolyl group, a 8-quinolyl group, a 1-isoquinolyl group, a3-isoquinolyl group, a 4-isoquinolyl group, a 5-isoquinolyl group, a6-isoquinolyl group, a 7-isoquinolyl group, a 8-isoquinolyl group, a2-quinoxalinyl group, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a4-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, a 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthroline-2-yl group,a 1,7-phenanthroline-3-yl group, a 1,7-phenanthroline-4-yl group, a1,7-phenanthroline-5-yl group, a 1,7-phenanthroline-6-yl group, a1,7-phenanthroline-8-yl group, a 1,7-phenanthroline-9-yl group, a1,7-phenanthroline-10-yl group, a 1,8-phenanthroline-2-yl group, a1,8-phenanthroline-3-yl group, a 1,8-phenanthroline-4-yl group, a1,8-phenanthroline-5-yl group, a 1,8-phenanthroline-6-yl group, a1,8-phenanthroline-7-yl group, a 1,8-phenanthroline-9-yl group, a1,8-phenanthroline-10-yl group, a 1,9-phenanthroline-2-yl group, a1,9-phenanthroline-3-yl group, a 1,9-phenanthroline-4-yl group, a1,9-phenanthroline-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthroline-8-yl group, a1,9-phenanthroline-10-yl group, a 1,10-phenanthroline-2-yl group, a1,10-phenanthroline-3-yl group, a 1,10-phenanthroline-4-yl group, a1,10-phenanthroline-5-yl group, a 2,9-phenanthroline-1-yl group, a2,9-phenanthroline-3-yl group, a 2,9-phenanthroline-4-yl group, a2,9-phenanthroline-5-yl group, a 2,9-phenanthroline-6-yl group, a2,9-phenanthroline-7-yl group, a 2,9-phenanthroline-8-yl group, a2,9-phenanthroline-10-yl group, a 2,8-phenanthroline-1-yl group, a2,8-phenanthroline-3-yl group, a 2,8-phenanthroline-4-yl group, a2,8-phenanthroline-5-yl group, a 2,8-phenanthroline-6-yl group, a2,8-phenanthroline-7-yl group, a 2,8-phenanthroline-9-yl group, a2,8-phenanthroline-10-yl group, a 2,7-phenanthroline-1-yl group, a2,7-phenanthroline-3-yl group, a 2,7-phenanthroline-4-yl group, a2,7-phenanthroline-5-yl group, a 2,7-phenanthroline-6-yl group, a2,7-phenanthroline-8-yl group, a 2,7-phenanthroline-9-yl group, a2,7-phenanthroline-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 1-phenoxazinylgroup, a 2-phenoxazinyl group, a 3-phenoxazinyl group, a 4-phenoxazinylgroup, a 2-oxazolyl group, a 4-oxazolyl group, a 5-oxazolyl group, a2-oxadiazolyl group, a 5-oxadiazolyl group, a 3-furazanyl group, a2-thienyl group, a 3-thienyl group, a 2-methylpyrrol-1-yl group, a2-methylpyrrol-3-yl group, a 2-methylpyrrol-4-yl group, a2-methylpyrrol-5-yl group, a 3-methylpyrrol-1-yl group, a3-methylpyrrol-2-yl group, a 3-methylpyrrol-4-yl group, a3-methylpyrrol-5-yl group, a 2-t-butylpyrrol-4-yl group, a3-(2-phenylpropyl)pyrrol-1-yl group, a 2-methyl-1-indolyl group, a4-methyl-1-indolyl group, a 2-methyl-3-indolyl group, a4-methyl-3-indolyl group, a 2-t-butyl 1-indolyl group, a 4-t-butyl1-indolyl group, a 2-t-butyl 3-indolyl group, and a 4-t-butyl 3-indolylgroup.

The alkoxycarbonyl group is represented by —COOY′. Examples of Y′ arethe same as the examples of the alkyl group.

The alkylamino group and the aralkylamino group are represented by—NQ¹Q². Examples for each of Q¹ and Q² are the same as the examplesdescribed in relation to the alkyl group and the aralkyl group, andpreferable examples for each of Q¹ and Q² are also the same as thosedescribed in relation to the alkyl group and the aralkyl group. Eitherone of Q¹ and Q² may be a hydrogen atom.

The arylamino group is represented by —NAr¹Ar². Examples for each of Ar¹and Ar² are the same as the examples described in relation to thenon-fused aryl group and the fused aryl group. Either one of Ar¹ and Ar²may be a hydrogen atom.

M represents aluminum (Al), gallium (Ga) or indium (In), among which Inis preferable.

L in the formula (A) represents a group represented by the followingformula (A′) or the following formula (A″).

In the formula, R⁸ to R¹² each independently represent a hydrogen atomor a substituted or unsubstituted hydrocarbon group having 1 to 40carbon atoms. Adjacent groups may form a cyclic structure. In theformula, R¹³ to R²⁷ each independently represent a hydrogen atom or asubstituted or unsubstituted hydrocarbon group having 1 to 40 carbonatoms. Adjacent groups may form a cyclic structure.

Examples of the hydrocarbon group having 1 to 40 carbon atomsrepresented by each of R⁸ to R¹² and R¹³ to R²⁷ in the formulae (A′) and(A″) are the same as those of R² to R⁷.

Examples of a divalent group formed when an adjacent set of R⁸ to R¹²and R¹³ to R²⁷ forms a cyclic structure are a tetramethylene group, apentamethylene group, a hexamethylene group, a diphenylmethane-2,2′-diylgroup, a diphenylethane-3,3′-diyl group, a diphenylpropane-4,4′-diylgroup and the like.

Examples of the nitrogen-containing cyclic metal chelate complexrepresented by the formula (A) will be shown below. However, thenitrogen-containing cyclic metal chelate complex is not limited to theexemplary compounds shown below.

According to the aspect of the invention, the electron injecting layerpreferably contains a nitrogen-containing heterocyclic derivative.

The electron injecting layer or the electron transporting layer, whichaids injection of the electrons into the emitting layer, has a highelectron mobility. The electron injecting layer is provided foradjusting energy level, by which, for instance, sudden changes of theenergy level can be reduced. As a material for the electron injectinglayer or the electron transporting layer, 8-hydroxyquinoline or a metalcomplex of its derivative, an oxadiazole derivative and anitrogen-containing heterocyclic derivative are preferable. An exampleof the 8-hydroxyquinoline or the metal complex of its derivative is ametal chelate oxinoid compound containing a chelate of oxine (typically8-quinolinol or 8-hydroxyquinoline). For instance, tris(8-quinolinol)aluminum can be used. Examples of the oxadiazole derivative are asfollows.

In the formula, Ar¹⁷, Ar¹⁸, Ar¹⁹, Ar²¹, Ar²² and Ar²⁵ each represent asubstituted or unsubstituted aryl group. Ar¹⁷, Ar¹⁹ and Ar²² may be thesame as or different from Ar¹⁸, Ar²¹ and Ar²⁵ respectively. Ar²⁰, Ar²³and Ar²⁴ each represent a substituted or unsubstituted arylene group.Ar²³ and Ar²⁴ may be mutually the same or different.

Examples of the arylene group are a phenylene group, naphthylene group,biphenylene group, anthranylene group, perylenylene group and pyrenylenegroup. Examples of the substituent therefor are an alkyl group having 1to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms and cyanogroup. Such an electron transport compound is preferably an electrontransport compound that can be favorably formed into a thin film(s).Examples of the electron transport compounds are as follows.

An example of the nitrogen-containing heterocyclic derivative is anitrogen-containing compound that is not a metal complex, the derivativebeing formed of an organic compound represented by one of the followinggeneral formulae. Examples of the nitrogen-containing heterocyclicderivative are five-membered ring or six-membered ring derivative havinga skeleton represented by the formula (A) and a derivative having astructure represented by the formula (B).

In the formula (B), X represents a carbon atom or nitrogen atom. Z₁ andZ₂ each independently represent an atom group capable of forming anitrogen-containing heterocycle.

Preferably, the nitrogen-containing heterocyclic derivative is anorganic compound having nitrogen-containing aromatic polycyclic serieshaving a five-membered ring or six-membered ring. When thenitrogen-containing heterocyclic derivative includes suchnitrogen-containing aromatic polycyclic series having plural nitrogenatoms, the nitrogen-containing heterocyclic derivative may be anitrogen-containing aromatic polycyclic organic compound having askeleton formed by a combination of the skeletons respectivelyrepresented by the formulae (A) and (B), or by a combination of theskeletons respectively represented by the formulae (A) and (C).

A nitrogen-containing group of the nitrogen-containing organic compoundis selected from nitrogen-containing heterocyclic groups respectivelyrepresented by the following general formulae.

In the formulae: R represents an aryl group having 6 to 40 carbon atoms,heteroaryl group having 3 to 40 carbon atoms, alkyl group having 1 to 20carbon atoms or alkoxy group having 1 to 20 carbon atoms; and nrepresents an integer of 0 to 5. When n is an integer of 2 or more,plural R may be mutually the same or different.

A preferable specific compound is a nitrogen-containing heterocyclicderivative represented by the following formula.

HAr-L¹-Ar¹⁻Ar²  [Chemical Formula 29]

In the formula, HAr represents a substituted or unsubstitutednitrogen-containing heterocycle having 3 to 40 carbon atoms; L¹represents a single bond, substituted or unsubstituted arylene grouphaving 6 to 40 carbon atoms or substituted or unsubstitutedheteroarylene group having 3 to 40 carbon atoms; Ar¹ represents asubstituted or unsubstituted divalent aromatic hydrocarbon group having6 to 40 carbon atoms; and Ar² represents a substituted or unsubstitutedaryl group having 6 to 40 carbon atoms or substituted or unsubstitutedheteroaryl group having 3 to 40 carbon atoms.

HAr is exemplarily selected from the following group.

L¹ is exemplarily selected from the following group.

Ar² is exemplarily selected from the following group.

Ar¹ is exemplarily selected from the following arylanthranil groups.

In the formula, R¹ to R¹⁴ each independently represent a hydrogen atom,a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxygroup having 1 to 20 carbon atoms, an aryloxy group having 6 to 40carbon atoms, a substituted or unsubstituted aryl group having 6 to 40carbon atoms, or a heteroaryl group having 3 to 40 carbon atoms. Ar³represents a substituted or unsubstituted aryl group having 6 to 40carbon atoms, or a heteroaryl group having 3 to 40 carbon atoms.

The nitrogen-containing heterocyclic derivative may be anitrogen-containing heterocyclic derivative in which R¹ to R⁸ in thestructure of Ar¹ represented by the above formula each represent ahydrogen atom.

Other than the above, the following compound (see JP-A-9-3448) can befavorably used.

In the formula, R₁ to R₄ each independently represent a hydrogen atom, asubstituted or unsubstituted aliphatic group, a substituted orunsubstituted alicyclic group, a substituted or unsubstitutedcarbocyclic aromatic ring group, or substituted or unsubstitutedheterocyclic group. X_(i) and X₂ each independently represent an oxygenatom, a sulfur atom or a dicyanomethylene group.

Alternatively, the following compound (see JP-A-2000-173774) can also befavorably used.

In the formula, R₁, R₂, R₃ and R₄, which may be mutually the same ordifferent, each represent an aryl group represented by the followingformula.

In the formula, R⁵, R⁶, R⁷, R⁸ and R⁹, which may be mutually the same ordifferent, each represent a hydrogen atom, a saturated or unsaturatedalkoxyl group, alkyl group, amino group or alkylamino group. At leastone of R⁵, R⁶, R⁷, R⁸ and R⁹ represents a saturated or unsaturatedalkoxyl group, alkyl group, amino group or alkylamino group.

A polymer compound containing the nitrogen-containing heterocyclic groupor a nitrogen-containing heterocyclic derivative may be used.

The electron transporting layer preferably contains at least one ofnitrogen-containing heterocycle derivatives respectively represented bythe following formulae (201) to (203).

In the formulae (201) to (203): R represents a hydrogen atom,substituted or unsubstituted aryl group having 6 to 60 carbon atoms,substituted or unsubstituted pyridyl group, substituted or unsubstitutedquinolyl group, substituted or unsubstituted alkyl group having 1 to 20carbon atoms or substituted or unsubstituted alkoxy group having 1 to 20carbon atoms; n represents an integer of 0 to 4; R¹ represents asubstituted or unsubstituted aryl group having 6 to 60 carbon atoms,substituted or unsubstituted pyridyl group, substituted or unsubstitutedquinolyl group, substituted or unsubstituted alkyl group having 1 to 20carbon atoms or alkoxy group having 1 to 20 carbon atoms; R² and R³ eachindependently represent a hydrogen atom, substituted or unsubstitutedaryl group having 6 to 60 carbon atoms, substituted or unsubstitutedpyrydyl group, substituted or unsubstituted quinolyl group, substitutedor unsubstituted alkyl group having 1 to 20 carbon atoms or substitutedor unsubstituted alkoxy group having 1 to 20 carbon atoms; L representsa substituted or unsubstituted arylene group having 6 to 60 carbonatoms, substituted or unsubstituted pyridinylene group, substituted orunsubstituted quinolinylene group or substituted or unsubstitutedfluorenylene group; Ar¹ represents a substituted or unsubstitutedarylene group having 6 to 60 carbon atoms, substituted or unsubstitutedpyridinylene group or substituted or unsubstituted quinolinylene group;Ar² represents a substituted or unsubstituted aryl group having 6 to 60carbon atoms, substituted or unsubstituted pyridyl group, substituted orunsubstituted quinolyl group, substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms or substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms.

Ar³ represents a substituted or unsubstituted aryl group having 6 to 60carbon atoms, substituted or unsubstituted pyridyl group, substituted orunsubstituted quinolyl group, substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms, substituted or unsubstituted alkoxy grouphaving 1 to 20 carbon atoms or a group represented by —Ar¹—Ar² (Ar¹ andAr² may be the same as the above).

In the formulae (201) to (203), R represents a hydrogen atom, asubstituted or unsubstituted aryl group having 6 to 60 carbon atoms, asubstituted or unsubstituted pyridyl group, substituted or unsubstitutedquinolyl group, a substituted or unsubstituted alkyl group having 1 to20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1to 20 carbon atoms.

The aryl group having 6 to 60 carbon atom is preferably an aryl grouphaving 6 to 40 carbon atoms, more preferably an aryl group having 6 to20 carbon atoms. Examples of such an aryl group are a phenyl group,naphthyl group, anthryl group, phenanthryl group, naphthacenyl group,chrysenyl group, pyrenyl group, biphenyl group, terphenyl group, tolylgroup, t-butylphenyl group, (2-phenylpropyl)phenyl group, fluoranthenylgroup, fluorenyl group, a monovalent group formed of spirobifluorene,perfluorophenyl group, perfluoronaphthyl group, perfluoroanthryl group,perfluorobiphenyl group, a monovalent group formed of9-phenylanthracene, a monovalent group formed of9-(1′naphthyl)anthracene, a monovalent group formed of9-(2′-naphthyl)anthracene, a monovalent group formed of6-phenylchrysene, and a monovalent group formed of 9-[4-(diphenylamine)phenyl]anthracene, among which a phenyl group, naphthyl group, biphenylgroup, terphenyl group, 9-(10-phenyl)anthryl group,9-[10-(1′-naphthyl)]anthryl group and 9-[10-(2′-naphthyl)]anthryl groupare preferable.

The alkyl group having 1 to 20 carbon atoms is preferably an alkyl grouphaving 1 to 6 carbon atoms. Examples of such an alkyl group are a methylgroup, ethyl group, propyl group, butyl group, pentyl group, hexylgroup, and a haloalkyl group such as trifluoromethyl group. When such analkyl group has 3 or more carbon atoms, the alkyl group may be linear,cyclic or branched.

The alkoxy group having 1 to 20 carbon atoms is preferably an alkoxygroup having 1 to 6 carbon atoms. Examples of such an alkoxy group are amethoxy group, ethoxy group, propoxy group, butoxy group, pentyloxygroup, and hexyloxy group. When such an alkoxy group has 3 or morecarbon atoms, the alkoxy group may be linear, cyclic or branched.

Examples of a substituent for the group represented by R are a halogenatom, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbonatoms, a substituted or unsubstituted aryloxy group having 6 to 40carbon atoms, a substituted or unsubstituted aryl group having 6 to 40carbon atoms, or a substituted or unsubstituted heteroaryl group having3 to 40 carbon atoms.

Examples of the halogen atom are fluorine, chlorine, bromine, iodine andthe like.

Examples for each of the alkyl group having 1 to 20 carbon atoms, thealkoxy group having 1 to 20 carbon atoms, and an aryl group having 6 to40 carbon atoms may be the same as the above examples.

Examples of the aryloxy group having 6 to 40 carbon atoms are a phenoxygroup and a biphenyloxy group.

Examples of the heteroaryl group having 3 to 40 carbon atoms are apyrrolyl group, furyl group, thienyl group, silolyl group, pyridylgroup, quinolyl group, isoquinolyl group, benzofuryl group, imidazolylgroup, pyrimidyl group, carbazolyl group, selenophenyl group,oxadiazolyl group and triazolyl group.

n is an integer in a range of 0 to 4, preferably 0 to 2.

In the formulae (201), R¹ represents a substituted or unsubstituted arylgroup having 6 to 60 carbon atoms, a substituted or unsubstitutedpyridyl group, a substituted or unsubstituted quinolyl group, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, oran alkoxy group having 1 to 20 carbon atoms.

Examples for each of the groups, the preferable number of carbon atomscontained in each of the groups, and preferable examples of thesubstituent for each of the groups are the same as those described inrelation to R.

In the formulae (202) and (203), R² and R³ each independently representa hydrogen atom, a substituted or unsubstituted aryl group having 6 to60 carbon atoms, a substituted or unsubstituted pyridyl group, asubstituted or unsubstituted quinolyl group, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, or a substitutedor unsubstituted alkoxy group having 1 to 20 carbon atoms.

Examples for each of the groups, the preferable number of carbon atomscontained in each of the groups, and preferable examples of thesubstituent for each of the groups are the same as those described inrelation to R.

In the formulae (201) to (203), L represents a substituted orunsubstituted arylene group having 6 to 60 carbon atoms, a substitutedor unsubstituted pyridinylene group, a substituted or unsubstitutedquinolinylene group, or a substituted or unsubstituted fluorenylenegroup.

The arylene group having 6 to 60 carbon atoms is preferably an arylenegroup having 6 to 40 carbon atoms, more preferably an arylene grouphaving 6 to 20 carbon atoms. An example of such an arylene group is adivalent group formed by removing one hydrogen atom from the aryl grouphaving been described in relation to R. Examples of a substituent forthe group represented by L are the same as those described in relationto R.

Alternatively, L is preferably a group selected from groups representedby the following formulae.

In the formulae (201), Ar¹ represents a substituted or unsubstitutedarylene group having 6 to 60 carbon atoms, a substituted orunsubstituted pyridinylene group, or a substituted or unsubstitutedquinolinylene group. Examples of a substituent for the groupsrepresented by Ar¹ and Ar² are the same as those described in relationto R.

Alternatively, Ar¹ is preferably selected from fused ring groupsrespectively represented by the following formulae (101) to (110).

In the formulae (101) to (110), the fused rings each may be linked witha link group formed of a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 40 carbon atoms, a substituted orunsubstituted aryl group having 6 to 40 carbon atoms or a substituted orunsubstituted heteroaryl group having 3 to 40 carbon atoms. When therings each are linked with plural link groups, the plural link groupsmay be mutually the same or different. Examples for each of the groupsare the same as those described above.

In the formula (110), L′ represents a single bond or a group selectedfrom groups represented by the following formulae.

The structure of Ar¹ represented by the formula (103) is preferably afused ring group represented by any one of the following formulae (111)to (125).

In the formulae (111) to (125), the fused rings each may be linked witha link group formed of a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 40 carbon atoms, a substituted orunsubstituted aryl group having 6 to 40 carbon atoms or a substituted orunsubstituted heteroaryl group having 3 to 40 carbon atoms. When therings each are linked with plural link groups, the plural link groupsmay be mutually the same or different. Examples for each of the groupsare the same as those described above.

In the formula (201), Ar² represents a substituted or unsubstituted arylgroup having 6 to 60 carbon atoms, a substituted or unsubstitutedpyridyl group, a substituted or unsubstituted quinolyl group, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

Examples for each of the groups, the preferable number of carbon atomscontained in each of the groups, and preferable examples of thesubstituent for each of the groups are the same as those described inrelation to R.

In the formulae (202) and (203), Ar³ represents a substituted orunsubstituted aryl group having 6 to 60 carbon atoms, a substituted orunsubstituted pyridyl group, a substituted or unsubstituted quinolylgroup, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbonatoms, or a group represented by —Ar¹—Ar² (Ar¹ and Ar² are the same asthe above).

Examples for each of the groups, the preferable number of carbon atomscontained in each of the groups, and preferable examples of thesubstituent for each of the groups are the same as those described inrelation to R.

Alternatively, Ar³ is preferably selected from fused ring groupsrespectively represented by the following formulae (126) to (135).

In the formulae (126) to (135), the fused rings each may be linked witha link group formed of a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 40 carbon atoms, a substituted orunsubstituted aryl group having 6 to 40 carbon atoms or a substituted orunsubstituted heteroaryl group having 3 to 40 carbon atoms. When therings each are linked with plural link groups, the plural link groupsmay be mutually the same or different. Examples for each of the groupsare the same as those described above.

In the formula (135), L′ represents the same as the above.

In the formulae (126) to (135), R′ represents a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 40 carbon atoms, ora substituted or unsubstituted heteroaryl group having 3 to 40 carbonatoms. Examples for each of the groups are the same as those describedabove.

The structure of Ar³ represented by the formula (128) is preferably afused ring group represented by any one of the following formulae (136)to (158).

In the formulae (136) to (158), the fused rings each may be linked witha link group formed of a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 40 carbon atoms, a substituted orunsubstituted aryl group having 6 to 40 carbon atoms or a substituted orunsubstituted heteroaryl group having 3 to 40 carbon atoms. When therings each are linked with plural link groups, the plural link groupsmay be mutually the same or different. Examples for each of the groupsare the same as those described above. R′ is the same as the above.

Alternatively, Ar² and Ar³ each independently are preferably a groupselected from groups represented by the following formulae.

Examples of the nitrogen-containing heterocyclic derivative representedby any one of the formulae (201) to (203) according to the aspect of theinvention will be shown below. However, the invention is not limited tothe exemplary compounds shown below.

In the chart shown below, HAr represents any one of the followingstructures respectively in the structures represented by the formulae(201) to (203).

[Chemical Formula 46] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 1-1

2

3

4

5

6

7

8

9

10

11

12

13

14

[Chemical Formula 47] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 2-1

2

3

4

5

6

7

8

9

[Chemical Formula 48] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 3-1

2

3

4

5

6

[Chemical Formula 49] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 4-1

2

3

4

5

6

7

8

9

10

11

12

[Chemical Formula 50] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 5-1

2

3

4

5

6

[Chemical Formula 51] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 6-1

2

3

4

5

[Chemical Formula 52] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 7-1

2

3

4

5

6

7

8

9

10

[Chemical Formula 53] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 8-1

2

3

4

5

6

7

8

9

10

11

12

13

[Chemical Formula 54] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 9-1

2

3

4

5

6

7

8

9

10

11

12

13

14

[Chemical Formula 55] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 10-1

2

3

4

5

6

7

8

9

[Chemical Formula 56] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 11-1

2

3

4

5

6

[Chemical Formula 57] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 12-1

2

3

4

5

6

7

8

9

10

11

[Chemical Formula 58] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 13-1

2

3

4

5

6

[Chemical Formula 59] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 14-1

2

3

4

5

[Chemical Formula 60] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 15-1

2

3

4

5

6

7

8

9

10

[Chemical Formula 61] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 16-1

2

3

4

5

6

7

8

[Chemical Formula 62] HAr—L—Ar¹—Ar² HAr L Ar¹ Ar² 17-1

2

3

4

5

6

7

8

Among the above examples, the compounds (1-1), (1-5), (1-7), (2-1),(3-1), (4-2), (4-6), (7-2), (7-7), (7-8), (7-9) and (9-7) areparticularly preferred.

Although thickness of the electron injecting layer or the electrontransporting layer is not specifically limited, the thickness ispreferably 1 to 100 nm.

The electron injecting layer preferably contains an inorganic compoundsuch as an insulator or a semiconductor in addition to thenitrogen-containing cyclic derivative. Such an insulator or asemiconductor, when contained in the electron injecting layer, caneffectively prevent a current leak, thereby enhancing electroninjectability of the electron injecting layer.

As the insulator, it is preferable to use at least one metal compoundselected from a group consisting of an alkali metal chalcogenide, analkali earth metal chalcogenide, a halogenide of alkali metal and ahalogenide of alkali earth metal. By forming the electron injectinglayer from the alkali metal chalcogenide or the like, the electroninjecting capability can preferably be further enhanced. Specifically,preferable examples of the alkali metal chalcogenide are Li₂O, K₂O,Na₂S, Na₂Se and Na₂O, while preferable example of the alkali earth metalchalcogenide are CaO, BaO, SrO, BeO, BaS and CaSe. Preferable examplesof the halogenide of the alkali metal are LiF, NaF, KF, LiCl, KCl andNaCl. Preferable examples of the halogenide of the alkali earth metalare fluorides such as CaF₂, BaF₂, SrF₂, MgF₂ and BeF₂, and halogenidesother than the fluoride.

Examples of the semiconductor are one of or a combination of two or moreof an oxide, a nitride or an oxidized nitride containing at least oneelement selected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si,Ta, Sb and Zn. An inorganic compound for forming the electron injectinglayer is preferably a microcrystalline or amorphous semiconductor film.When the electron injecting layer is formed of such semiconductor film,more uniform thin film can be formed, thereby reducing pixel defectssuch as a dark spot. Examples of such an inorganic compound are theabove-described alkali metal chalcogenide, alkali earth metalchalcogenide, halogenide of the alkali metal and halogenide of thealkali earth metal.

The electron injecting layer in the aspect of the invention maypreferably contain the above-described reduction-causing dopant.

The hole injecting layer or the hole transporting layer (including thehole injecting/transporting layer) may contain an aromatic aminecompound such as an aromatic amine derivative represented by thefollowing (I).

In the above formula (I), Ar¹ to Ar⁴ represent a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms or asubstituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

Examples of the substituted or unsubstituted aryl group having 6 to 50ring carbon atoms include a phenyl group, a 1-naphthyl group, a2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthrylgroup, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthrylgroup, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenylgroup, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenylgroup, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, a 4′-t-butyl-p-terphenyl-4-yl group, afluoranthenyl group, and a fluorenyl group.

Examples of the substituted or unsubstituted heteroaryl group having 5to 50 ring atoms include a 1-pyrrolyl group, a 2-pyrrolyl group, a3-pyrrolyl group, a pyrazinyl group, a 2-pyrizinyl group, a 3-pyrizinylgroup, a 4-pyrizinyl group, a 1-indolyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolyl group, a3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group,a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group,a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a7-isoquinolyl group, a 8-isoquinolyl group, a 2-quinoxalinyl group, a5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, a 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthroline-2-yl group,a 1,7-phenanthroline-3-yl group, a 1,7-phenanthroline-4-yl group, a1,7-phenanthroline-5-yl group, a 1,7-phenanthroline-6-yl group, a1,7-phenanthroline-8-yl group, a 1,7-phenanthroline-9-yl group, a1,7-phenanthroline-10-yl group, a 1,8-phenanthroline-2-yl group, a1,8-phenanthroline-3-yl group, a 1,8-phenanthroline-4-yl group, a1,8-phenanthroline-5-yl group, a 1,8-phenanthroline-6-yl group, a1,8-phenanthroline-7-yl group, a 1,8-phenanthroline-9-yl group, a1,8-phenanthroline-10-yl group, a 1,9-phenanthroline-2-yl group, a1,9-phenanthroline-3-yl group, a 1,9-phenanthroline-4-yl group, a1,9-phenanthroline-5-yl group, a 1,9-phenanthroline-6-yl group, a1,9-phenanthroline-7-yl group, a 1,9-phenanthroline-8-yl group, a1,9-phenanthroline-10-yl group, a 1,10-phenanthroline-2-yl group, a1,10-phenanthroline-3-yl group, a 1,10-phenanthroline-4-yl group, a1,10-phenanthroline-5-yl group, a 2,9-phenanthroline-1-yl group, a2,9-phenanthroline-3-yl group, a 2,9-phenanthroline-4-yl group, a2,9-phenanthroline-5-yl group, a 2,9-phenanthroline-6-yl group, a2,9-phenanthroline-7-yl group, a 2,9-phenanthroline-8-yl group, a2,9-phenanthroline-10-yl group, a 2,8-phenanthroline-1-yl group, a2,8-phenanthroline-3-yl group, a 2,8-phenanthroline-4-yl group, a2,8-phenanthroline-5-yl group, a 2,8-phenanthroline-6-yl group, a2,8-phenanthroline-7-yl group, a 2,8-phenanthroline-9-yl group, a2,8-phenanthroline-10-yl group, a 2,7-phenanthroline-1-yl group, a2,7-phenanthroline-3-yl group, a 2,7-phenanthroline-4-yl group, a2,7-phenanthroline-5-yl group, a 2,7-phenanthroline-6-yl group, a2,7-phenanthroline-8-yl group, a 2,7-phenanthroline-9-yl group, a2,7-phenanthroline-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a 4-t-butyl 1-indolyl group, a 2-t-butyl 3-indolylgroup, and a 4-t-butyl 3-indolyl group. Preferred are a phenyl group, anaphthyl group, a biphenyl group, an anthranil group, a phenanthrylgroup, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, afluorenyl group and the like.

L indicates a linking group. The examples are a divalent group obtainedby linking a substituted or unsubstituted arylene group having 6 to 50ring carbon atoms, a substituted or unsubstituted heteroarylene grouphaving 5 to 50 ring atoms, or at least two arylene groups orheteroarylene groups via a single bond, an ether bond, a thioether bond,an alkylene group having 1 to 20 carbon atoms, an alkenylene grouphaving 2 to 20 carbon atoms, or an amino group. Examples of the arylenegroup having 6 to 50 ring carbon atoms include a 1,4-phenylene group, a1,2-phenylene group, a 1,3-phenylene group, a 1,4-naphthylene group, a2,6-naphthylene group, a 1,5-naphthylene group, a 9,10-anthranylenegroup, a 9,10-phenanthrenylene group, a 3,6-phenanthrenylene group, a1,6-pyrenylene group, a 2,7-pyrenylene group, a 6,12-chrysenylene group,a 4,4′-biphenylene group, a 3,3′-biphenylene group, a 2,2′-biphenylenegroup, and a 2,7-fluorenylene group. Examples of the arylene grouphaving 5 to 50 ring atoms include a 2,5-thiophenylene group, a2,5-silolylene group, and a 2,5-oxadiazolylene group. Preferably, thearylene group is 1,4-phenylene group, a 1,2-phenylene group, a1,3-phenylene group, a 1,4-naphthylene group, a 9,10-anthranylene group,a 6,12-chrysenylene group, a 4,4′-biphenylene group, a 3,3′-biphenylenegroup, a 2,2′-biphenylene group, or a 2,7-fluorenylene group.

When L is a linking group consisting of two or more arylene groups orheteroarylene groups, the arylene groups or heteroarylene groupsadjacent to each other may form a new ring by bonding to each other viaa divalent group. Examples of the divalent group for forming a ringinclude a tetramethylene group, a pentamethylene group, a hexamethylenegroup, a diphenylmethane-2,2′-diyl group, a diphenylethane-3,3′-diylgroup, and a diphenylpropane-4,4′-diyl group.

Examples of the substituent group of Ar¹ to Ar⁴ and L include asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, a substituted or unsubstituted heteroaryl group having 5 to 50ring atoms, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1to 50 carbon atoms, a substituted or unsubstituted aralkyl group having7 to 50 carbon atoms, a substituted or unsubstituted aryloxy grouphaving 6 to 50 ring carbon atoms, a substituted or unsubstitutedheteroaryloxy group having 5 to 50 ring atoms, a substituted orunsubstituted arylthio group having 6 to 50 ring carbon atoms, asubstituted or unsubstituted heteroarylthio group having 5 to 50 ringatoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to50 carbon atoms, an amino group which is substituted with a substitutedor unsubstituted aryl group having 6 to 50 ring carbon atoms or aheteroaryl group having 5 to 50 ring atoms, a halogen atom, cyano group,a nitro group, and a hydroxy group.

Examples of the substituted or unsubstituted aryl group having 6 to 50ring carbon atoms include a phenyl group, a 1-naphthyl group, a2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthrylgroup, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthrylgroup, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenylgroup, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenylgroup, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, a 4′-t-butyl-p-terphenyl-4-yl group, afluoranthenyl group, and a fluorenyl group.

Examples of the substituted or unsubstituted heteroaryl group having 5to 50 ring atoms include a 1-pyrrolyl group, a 2-pyrrolyl group, a3-pyrrolyl group, a pyrazinyl group, a 2-pyrizinyl group, a 3-pyrizinylgroup, a 4-pyrizinyl group, a 1-indolyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 2-isoindolyl group, a3-isoindolyl group, a 4-isoindolyl group, a 5-isoindolyl group, a6-isoindolyl group, a 7-isoindolyl group, a 2-furyl group, a 3-furylgroup, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranylgroup, a 5-benzofuranyl group, a 6-benzofuranyl group, a 7-benzofuranylgroup, a 1-isobenzofuranyl group, a 3-isobenzofuranyl group, a4-isobenzofuranyl group, a 5-isobenzofuranyl group, a 6-isobenzofuranylgroup, a 7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group,a 4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group,a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a7-isoquinolyl group, a 8-isoquinolyl group, a 2-quinoxalinyl group, a5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, a 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthroline-2-yl group,a 1,7-phenanthroline-3-yl group, a 1,7-phenanthroline-4-yl group, a1,7-phenanthroline-5-yl group, a 1,7-phenanthroline-6-yl group, a1,7-phenanthroline-8-yl group, a 1,7-phenanthroline-9-yl group, a1,7-phenanthroline-10-yl group, a 1,8-phenanthroline-2-yl group, a1,8-phenanthroline-3-yl group, a 1,8-phenanthroline-4-yl group, a1,8-phenanthroline-5-yl group, a 1,8-phenanthroline-6-yl group, a1,8-phenanthroline-7-yl group, a 1,8-phenanthroline-9-yl group, a1,8-phenanthroline-10-yl group, a 1,9-phenanthroline-2-yl group, a1,9-phenanthroline-3-yl group, a 1,9-phenanthroline-4-yl group, a1,9-phenanthroline-5-yl group, a 1,9-phenanthroline-6-yl group, a1,9-phenanthroline-7-yl group, a 1,9-phenanthroline-8-yl group, a1,9-phenanthroline-10-yl group, a 1,10-phenanthroline-2-yl group, a1,10-phenanthroline-3-yl group, a 1,10-phenanthroline-4-yl group, a1,10-phenanthroline-5-yl group, a 2,9-phenanthroline-1-yl group, a2,9-phenanthroline-3-yl group, a 2,9-phenanthroline-4-yl group, a2,9-phenanthroline-5-yl group, a 2,9-phenanthroline-6-yl group, a2,9-phenanthroline-7-yl group, a 2,9-phenanthroline-8-yl group, a2,9-phenanthroline-10-yl group, a 2,8-phenanthroline-1-yl group, a2,8-phenanthroline-3-yl group, a 2,8-phenanthroline-4-yl group, a2,8-phenanthroline-5-yl group, a 2,8-phenanthroline-6-yl group, a2,8-phenanthroline-7-yl group, a 2,8-phenanthroline-9-yl group, a2,8-phenanthroline-10-yl group, a 2,7-phenanthroline-1-yl group, a2,7-phenanthroline-3-yl group, a 2,7-phenanthroline-4-yl group, a2,7-phenanthroline-5-yl group, a 2,7-phenanthroline-6-yl group, a2,7-phenanthroline-8-yl group, a 2,7-phenanthroline-9-yl group, a2,7-phenanthroline-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a 4-t-butyl 1-indolyl group, a 2-t-butyl 3-indolylgroup, and a 4-t-butyl 3-indolyl group.

Examples of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms include a methyl group, an ethyl group, a propyl group, anisopropyl group, an n-butyl group, an s-butyl group, an isobutyl group,a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group,an n-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted cycloalkyl group having 3to 50 carbon atoms include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a2-norbornyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms is a group represented by —OY. Examples of Y include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted aralkyl group having 7 to50 carbon atoms include a benzyl group, a 1-phenylethyl group, a2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropylgroup, a phenyl-t-butyl group, a α-naphthylmethyl group, a1-α-naphthylethyl group, a 2-α-naphthylethyl group, a1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, aβ-naphthylmethyl group, a 1-3-naphthylethyl group, a 2-β-naphthylethylgroup, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, a1-pyrrolylmethyl group, a 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, an o-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group.

The substituted or unsubstituted aryloxy group having 6 to 50 ringcarbon atoms is represented by —OY′. Examples of Y′ include a phenylgroup, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4′-t-butyl-p-terphenyl-4-yl group.

The substituted or unsubstituted heteroaryloxy group having 5 to 50 ringatoms is represented by —OZ′. Examples of Z′ include a 2-pyrrolyl group,a 3-pyrrolyl group, a pyrazinyl group, a 2-pyrizinyl group, a3-pyrizinyl group, a 4-pyrizinyl group, a 2-indolyl group, a 3-indolylgroup, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group, a7-indolyl group, a 1-isoindolyl group, a 3-isoindolyl group, a4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group,a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a7-isoquinolyl group, a 8-isoquinolyl group, a 2-quinoxalinyl group, a5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinylgroup, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a7-phenanthridinyl group, a 8-phenanthridinyl group, a 9-phenanthridinylgroup, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinylgroup, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a1,7-phenanthroline-2-yl group, a 1,7-phenanthroline-3-yl group, a1,7-phenanthroline-4-yl group, a 1,7-phenanthroline-5-yl group, a1,7-phenanthroline-6-yl group, a 1,7-phenanthroline-8-yl group, a1,7-phenanthroline-9-yl group, a 1,7-phenanthroline-10-yl group, a1,8-phenanthroline-2-yl group, a 1,8-phenanthroline-3-yl group, a1,8-phenanthroline-4-yl group, a 1,8-phenanthroline-5-yl group, a1,8-phenanthroline-6-yl group, a 1,8-phenanthroline-7-yl group, a1,8-phenanthroline-9-yl group, a 1,8-phenanthroline-10-yl group, a1,9-phenanthroline-2-yl group, a 1,9-phenanthroline-3-yl group, a1,9-phenanthroline-4-yl group, a 1,9-phenanthroline-5-yl group, a1,9-phenanthroline-6-yl group, a 1,9-phenanthroline-7-yl group, a1,9-phenanthroline-8-yl group, a 1,9-phenanthroline-10-yl group, a1,10-phenanthroline-2-yl group, a 1,10-phenanthroline-3-yl group, a1,10-phenanthroline-4-yl group, a 1,10-phenanthroline-5-yl group, a2,9-phenanthroline-1-yl group, a 2,9-phenanthroline-3-yl group, a2,9-phenanthroline-4-yl group, a 2,9-phenanthroline-5-yl group, a2,9-phenanthroline-6-yl group, a 2,9-phenanthroline-7-yl group, a2,9-phenanthroline-8-yl group, a 2,9-phenanthroline-10-yl group, a2,8-phenanthroline-1-yl group, a 2,8-phenanthroline-3-yl group, a2,8-phenanthroline-4-yl group, a 2,8-phenanthroline-5-yl group, a2,8-phenanthroline-6-yl group, a 2,8-phenanthroline-7-yl group, a2,8-phenanthroline-9-yl group, a 2,8-phenanthroline-10-yl group, a2,7-phenanthroline-1-yl group, a 2,7-phenanthroline-3-yl group, a2,7-phenanthroline-4-yl group, a 2,7-phenanthroline-5-yl group, a2,7-phenanthroline-6-yl group, a 2,7-phenanthroline-8-yl group, a2,7-phenanthroline-9-yl group, a 2,7-phenanthroline-10-yl group, a1-phenazinyl group, a 2-phenazinyl group, a 1-phenothiazinyl group, a2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a 4-t-butyl 1-indolyl group, a 2-t-butyl 3-indolylgroup, and a 4-t-butyl 3-indolyl group.

The substituted or unsubstituted arylthio group having 6 to 50 ringcarbon atoms is represented by —SY″. Examples of Y″ include a phenylgroup, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a9-phenanthryl group, a 1-naphthacenyl group, a 2-naphthacenyl group, a9-naphthacenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenylgroup, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group,a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-ylgroup, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, anm-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolylgroup, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, and a4′-t-butyl-p-terphenyl-4-yl group.

The substituted or unsubstituted heteroarylthio group having 5 to 50ring atoms is represented by —SZ″, and examples of Z″ include a2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyrizinylgroup, a 3-pyrizinyl group, a 4-pyrizinyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolyl group, a4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group,a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a7-isoquinolyl group, a 8-isoquinolyl group, a 2-quinoxalinyl group, a5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinylgroup, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a7-phenanthridinyl group, a 8-phenanthridinyl group, a 9-phenanthridinylgroup, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinylgroup, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a1,7-phenanthroline-2-yl group, a 1,7-phenanthroline-3-yl group, a1,7-phenanthroline-4-yl group, a 1,7-phenanthroline-5-yl group, a1,7-phenanthroline-6-yl group, a 1,7-phenanthroline-8-yl group, a1,7-phenanthroline-9-yl group, a 1,7-phenanthroline-10-yl group, a1,8-phenanthroline-2-yl group, a 1,8-phenanthroline-3-yl group, a1,8-phenanthroline-4-yl group, a 1,8-phenanthroline-5-yl group, a1,8-phenanthroline-6-yl group, a 1,8-phenanthroline-7-yl group, a1,8-phenanthroline-9-yl group, a 1,8-phenanthroline-10-yl group, a1,9-phenanthroline-2-yl group, a 1,9-phenanthroline-3-yl group, a1,9-phenanthroline-4-yl group, a 1,9-phenanthroline-5-yl group, a1,9-phenanthroline-6-yl group, a 1,9-phenanthroline-7-yl group, a1,9-phenanthroline-8-yl group, a 1,9-phenanthroline-10-yl group, a1,10-phenanthroline-2-yl group, a 1,10-phenanthroline-3-yl group, a1,10-phenanthroline-4-yl group, a 1,10-phenanthroline-5-yl group, a2,9-phenanthroline-1-yl group, a 2,9-phenanthroline-3-yl group, a2,9-phenanthroline-4-yl group, a 2,9-phenanthroline-5-yl group, a2,9-phenanthroline-6-yl group, a 2,9-phenanthroline-7-yl group, a2,9-phenanthroline-8-yl group, a 2,9-phenanthroline-10-yl group, a2,8-phenanthroline-1-yl group, a 2,8-phenanthroline-3-yl group, a2,8-phenanthroline-4-yl group, a 2,8-phenanthroline-5-yl group, a2,8-phenanthroline-6-yl group, a 2,8-phenanthroline-7-yl group, a2,8-phenanthroline-9-yl group, a 2,8-phenanthroline-10-yl group, a2,7-phenanthroline-1-yl group, a 2,7-phenanthroline-3-yl group, a2,7-phenanthroline-4-yl group, a 2,7-phenanthroline-5-yl group, a2,7-phenanthroline-6-yl group, a 2,7-phenanthroline-8-yl group, a2,7-phenanthroline-9-yl group, a 2,7-phenanthroline-10-yl group, a1-phenazinyl group, a 2-phenazinyl group, a 1-phenothiazinyl group, a2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a 4-t-butyl 1-indolyl group, a 2-t-butyl 3-indolylgroup, and a 4-t-butyl 3-indolyl group.

The substituted or unsubstituted alkoxycarbonyl group having 2 to 50carbon atoms is represented by —COOZ. Examples of Z include a methylgroup, an ethyl group, a propyl group, an isopropyl group, an n-butylgroup, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentylgroup, an n-hexyl group, an n-heptyl group, an n-octyl group, ahydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chloroethylgroup, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a2,3-dichloro-t-butyl group, a 1,2,3-trichloropropyl group, a bromomethylgroup, a 1-bromoethyl group, a 2-bromoethyl group, a 2-bromoisobutylgroup, a 1,2-dibromoethyl group, a 1,3-dibromoisopropyl group, a2,3-dibromo-t-butyl group, a 1,2,3-tribromopropyl group, an iodomethylgroup, a 1-iodoethyl group, a 2-iodoethyl group, a 2-iodoisobutyl group,a 1,2-diiodoethyl group, a 1,3-diiodoisopropyl group, a2,3-diiodo-t-butyl group, a 1,2,3-triiodopropyl group, an aminomethylgroup, a 1-aminoethyl group, a 2-aminoethyl group, a 2-aminoisobutylgroup, a 1,2-diaminoethyl group, a 1,3-diaminoisopropyl group, a2,3-diamino-t-butyl group, a 1,2,3-triaminopropyl group, a cyanomethylgroup, a 1-cyanoethyl group, a 2-cyanoethyl group, a 2-cyanoisobutylgroup, a 1,2-dicyanoethyl group, a 1,3-dicyanoisopropyl group, a2,3-dicyano-t-butyl group, a 1,2,3-tricyanopropyl group, a nitromethylgroup, a 1-nitroethyl group, a 2-nitroethyl group, a 2-nitroisobutylgroup, a 1,2-dinitroethyl group, a 1,3-dinitroisopropyl group, a2,3-dinitro-t-butyl group, and a 1,2,3-trinitropropyl group.

The amino group which is substituted with a substituted or unsubstitutedaryl group having 6 to 50 ring carbon atoms or with a substituted orunsubstituted heteroaryl group having 5 to 50 ring atoms is representedby —NPQ. Examples of P and Q include a phenyl group, a 1-naphthyl group,a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthrylgroup, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthrylgroup, a 4-phenanthryl group, a 9-phenanthryl group, a 1-naphthacenylgroup, a 2-naphthacenyl group, a 9-naphthacenyl group, a 1-pyrenylgroup, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylyl group, a3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-yl group, ap-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-ylgroup, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolylgroup, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, ap-(2-phenylpropyl)phenyl group, a 3-methyl-2-naphthyl group, a4-methyl-1-naphthyl group, a 4-methyl-1-anthryl group, a4′-methylbiphenylyl group, a 4′-t-butyl-p-terphenyl-4-yl group, a2-pyrrolyl group, a 3-pyrrolyl group, a pyrazinyl group, a 2-pyrizinylgroup, a 3-pyrizinyl group, a 4-pyrizinyl group, a 2-indolyl group, a3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolylgroup, a 7-indolyl group, a 1-isoindolyl group, a 3-isoindolyl group, a4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a 2-quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, a 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group,a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolyl group, a7-isoquinolyl group, a 8-isoquinolyl group, a 2-quinoxalinyl group, a5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolyl group, a2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, a1-phenanthridinyl group, a 2-phenanthridinyl group, a 3-phenanthridinylgroup, a 4-phenanthridinyl group, a 6-phenanthridinyl group, a7-phenanthridinyl group, a 8-phenanthridinyl group, a 9-phenanthridinylgroup, a 10-phenanthridinyl group, a 1-acridinyl group, a 2-acridinylgroup, a 3-acridinyl group, a 4-acridinyl group, a 9-acridinyl group, a1,7-phenanthroline-2-yl group, a 1,7-phenanthroline-3-yl group, a1,7-phenanthroline-4-yl group, a 1,7-phenanthroline-5-yl group, a1,7-phenanthroline-6-yl group, a 1,7-phenanthroline-8-yl group, a1,7-phenanthroline-9-yl group, a 1,7-phenanthroline-10-yl group, a1,8-phenanthroline-2-yl group, a 1,8-phenanthroline-3-yl group, a1,8-phenanthroline-4-yl group, a 1,8-phenanthroline-5-yl group, a1,8-phenanthroline-6-yl group, a 1,8-phenanthroline-7-yl group, a1,8-phenanthroline-9-yl group, a 1,8-phenanthroline-10-yl group, a1,9-phenanthroline-2-yl group, a 1,9-phenanthroline-3-yl group, a1,9-phenanthroline-4-yl group, a 1,9-phenanthroline-5-yl group, a1,9-phenanthroline-6-yl group, a 1,9-phenanthroline-7-yl group, a1,9-phenanthroline-8-yl group, a 1,9-phenanthroline-10-yl group, a1,10-phenanthroline-2-yl group, a 1,10-phenanthroline-3-yl group, a1,10-phenanthroline-4-yl group, a 1,10-phenanthroline-5-yl group, a2,9-phenanthroline-1-yl group, a 2,9-phenanthroline-3-yl group, a2,9-phenanthroline-4-yl group, a 2,9-phenanthroline-5-yl group, a2,9-phenanthroline-6-yl group, a 2,9-phenanthroline-7-yl group, a2,9-phenanthroline-8-yl group, a 2,9-phenanthroline-10-yl group, a2,8-phenanthroline-1-yl group, a 2,8-phenanthroline-3-yl group, a2,8-phenanthroline-4-yl group, a 2,8-phenanthroline-5-yl group, a2,8-phenanthroline-6-yl group, a 2,8-phenanthroline-7-yl group, a2,8-phenanthroline-9-yl group, a 2,8-phenanthroline-10-yl group, a2,7-phenanthroline-1-yl group, a 2,7-phenanthroline-3-yl group, a2,7-phenanthroline-4-yl group, a 2,7-phenanthroline-5-yl group, a2,7-phenanthroline-6-yl group, a 2,7-phenanthroline-8-yl group, a2,7-phenanthroline-9-yl group, a 2,7-phenanthroline-10-yl group, a1-phenazinyl group, a 2-phenazinyl group, a 1-phenothiazinyl group, a2-phenothiazinyl group, a 3-phenothiazinyl group, a 4-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 2-oxazolyl group, a 4-oxazolyl group, a5-oxazolyl group, a 2-oxadiazolyl group, a 5-oxadiazolyl group, a3-furazanyl group, a 2-thienyl group, a 3-thienyl group, a2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl)pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a 2-t-butyl1-indolyl group, a 4-t-butyl 1-indolyl group, a 2-t-butyl 3-indolylgroup, and a 4-t-butyl 3-indolyl group.

Examples of the compound represented by the formula (I) are shown below.However, the compound is not limited thereto.

Aromatic amine represented by the following general formula (II) canalso be preferably used for forming the hole injecting layer or the holetransporting layer.

In the formula (II), Ar¹ to Ar³ each represent the same as thoserepresented by Ar¹ to Ar⁴ of the above formula (I). Examples of thecompound represented by the general formula (II) are shown below.However, the compound represented by the formula (II) is not limitedthereto.

The anode of the organic EL device is used for injecting holes into thehole transporting layer or the emitting layer. It is effective that theanode has a work function of 4.5 eV or more. Exemplary materials for theanode for use in the aspect of the invention are indium-tin oxide (ITO),tin oxide (NESA), gold, silver, platinum and copper. The cathode ispreferably formed of a material with smaller work function in order toinject electrons into the electron injecting layer or the emittinglayer. Although a material for the cathode is subject to no specificlimitation, examples of the material are indium, aluminum, magnesium,alloy of magnesium and indium, alloy of magnesium and aluminum, alloy ofaluminum and lithium, alloy of aluminum, scandium and lithium, alloy ofmagnesium and silver and the like.

A method of forming each of the layers in the organic EL deviceaccording to the aspect of the invention is not particularly limited. Aconventionally-known methods such as vacuum deposition or spin coatingmay be employed for forming the layers. The organic thin-film layercontaining the compound represented by the formula (1), which is used inthe organic EL device according to the aspect of the invention, may beformed by a conventional coating method such as vacuum deposition,molecular beam epitaxy (MBE method) and coating methods using a solutionsuch as a dipping, spin coating, casting, bar coating, and roll coating.

Although the thickness of each organic layer of the organic EL device isnot particularly limited, the thickness is generally preferably in arange of several nanometers to 1 μm because an excessively-thinned filmlikely entails defects such as a pin hole while an excessively-thickenedfilm requires high voltage to be applied and deteriorates efficiency.

The organic EL device is formed on a light-transmissive substrate. Thelight-transmissive substrate, which supports the organic EL device, ispreferably a smoothly-shaped substrate that transmits 50% or more oflight in a visible region of 400 nm to 700 nm.

The light-transmissive substrate is exemplarily a glass plate, a polymerplate or the like.

For the glass plate, materials such as soda-lime glass,barium/strontium-containing glass, lead glass, aluminosilicate glass,borosilicate glass, barium borosilicate glass and quartz can be used.

For the polymer plate, materials such as polycarbonate, acryl,polyethylene terephthalate, polyether sulfide and polysulfone can beused.

Synthesis Example

Next, the invention will be described in further detail with referenceto synthesis reference(s) and synthesis example(s). However, theinvention is not limited to such synthesis examples.

[Synthesis Reference 1-1] Synthesis of 2-(3-bromophenyl)naphthalene

Under an argon gas atmosphere, 243 g (1.41 mol) of 2-naphthaleneboronicacid, 400 g (1.41 mol) of 3-bromoiodobenzene, 3.27 g (28.2 mmol) oftetrakis(triphenylphosphine)palladium(0), 6.4 L of toluene and 3.2 L ofaqueous solution of 2M sodium carbonate were added together, and stirredwhile being refluxed for 24 hours. After the reaction was over, themixture experienced filtration, through which aqueous phase thereof waseliminated. After organic phase thereof was washed by water and driedwith magnesium sulfate, the toluene was distilled away under reducedpressure. Residue thereof was refined by silica-gel columnchromatography, such that 303 g of 2-(3-bromophenyl)naphthalene wasobtained at an yield of 76%.

[Synthesis Reference 1-2] Synthesis of 3-(2-naphthyl)phenylboronic acid

Under an argon gas atmosphere, a mixture of 212 g (748 mmol) of2(3-bromophenyl)naphthalene and 3 L of dehydrated TI-IF was cooled downto minus 10 degree C., and 600 ml (948 mmol) of hexane solution of 1.6Mn-butyllithium was dropped into the mixture while the mixture was beingstirred. Then, the mixture was stirred at 0 degree C. for 2 hours. Thereaction solution was again cooled down to minus 78 degrees C., and 450g (2.39 mol) of triisopropylborate was dropped into the solution. Then,the solution was stirred at room temperature for 17 hours. The reactionmixture was added with aqueous solution of hydrochloric acid and stirredat room temperature for 1 hour. The reaction mixture was added with 3 Lof toluene, and aqueous phase thereof was eliminated. After organicphase thereof was dried with magnesium sulfate, the solvent wasdistilled away under reduced pressure. By recrystallizing the obtainedsolid by toluene, 126 g of 3-(2-naphthyl)phenylboronic acid was obtainedat an yield of 67%.

[Synthesis Reference 2-1] Synthesis of 2-(3-bromophenyl)naphthalene

Under an argon gas atmosphere, 70.0 g (407 mmol) of 2-naphthaleneboronicacid, 115.10 g (407 mmol) of 4-bromoiodobenzene, 9.40 g (8.14 mmol) oftetrakis(triphenylphosphine)palladium(0), 1.2 L of toluene and 600 mL ofaqueous solution of 2M sodium carbonate were added together, and stirredat 90 degrees C. for 20 hours. After the reaction was over, toluene wasdistilled away and methanol was added. Then, the precipitated solid wasseparated by filtration. The obtained solid was recrystallized withacetic ether and methanol and dried. 77.2 g of2-(4-bromophenyl)naphthalene was obtained at an yield of 67%.

[Synthesis Reference 2-2] Synthesis of 4-(2-naphthyl)phenylboronic acid

Under an argon gas atmosphere, a mixture of 50.0 g (177 mmol) of2(4-bromophenyl)naphthalene and 500 mL of dehydrated THF was cooled downto minus 60 degree C. Then, 136 ml (212 mmol) of hexane solution of1.56M n-butyllithium was dropped into the mixture while the mixture wasbeing stirred. The reaction mixture was further stirred at minus 60degrees for 1 hour. 99.6 g (529 mmol) of triisopropylborate was droppedinto the reaction mixture at minus 60 degrees C. Subsequently, thereaction mixture was warmed up to room temperature, and stirred for 18hours. The reaction mixture was added with aqueous solution ofhydrochloric acid and stirred at room temperature for 1 hour. After thereaction, the reaction mixture was added with toluene, and aqueous phasethereof was eliminated. Then, organic phase thereof was dried withmagnesium sulfate, and the solvent was distilled away under reducedpressure. By recrystallizing the obtained solid by toluene, 33.6 g of4-(2-naphthyl)phenylboronic acid was obtained at an yield of 84%.

[Synthesis Reference 3-1] Synthesis of 1-(3-bromophenyl)naphthalene

Under an argon gas atmosphere, 200.0 g (1.163 mol) of1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 3-bromoiodobenzene,26.9 g (23.3 mmol) of tetrakis(triphenylphosphine)palladium(0), 3.7 L oftoluene and 1.74 L of aqueous solution of 2M sodium carbonate were addedtogether, and stirred while being refluxed for 24 hours. After thereaction was over, the mixture experienced filtration, through whichaqueous phase thereof was eliminated. After organic phase thereof waswashed by water and dried with magnesium sulfate, the toluene wasdistilled away under reduced pressure. Residue thereof was refined bysilica-gel column chromatography, such that 250 g of1-(3-bromophenyl)naphthalene was obtained at an yield of 76%.

[Synthesis Reference 3-2] Synthesis of 3-(1-naphthyl)phenylboronic acid

Under an argon gas atmosphere, a mixture of 200.0 g (706.3 mmol) of1-(3-bromophenyl)naphthalene and 2.1 L of dehydrated THF was cooled downto minus 60 degree C. Then, 543 ml (847 mmol) of hexane solution of1.56M n-butyllithium was dropped into the mixture while the mixture wasbeing stirred. The reaction mixture was further stirred at minus 60degrees for 2 hours. The reaction solution was again cooled down tominus 60 degrees C., and 398.5 g (2.119 mol) of triisopropylborate wasdropped into the solution. Subsequently, the reaction mixture was warmedup to room temperature, and stirred for 17 hours. The reaction mixturewas added with aqueous solution of hydrochloric acid and stirred at roomtemperature for 1 hour. After the reaction, the reaction mixture wasadded with toluene, and aqueous phase thereof was eliminated. Then,organic phase thereof was dried with magnesium sulfate, and the solventwas distilled away under reduced pressure. By recrystallizing theobtained solid by toluene, 126 g of 3-(1-naphthyl)phenylboronic acid wasobtained at an yield of 67%.

[Synthesis Reference 4-1] Synthesis of 1-(4-bromophenyl)naphthalene

Under an argon gas atmosphere, 200.0 g (1.163 mol) of1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 4-bromoiodobenzene,26.9 g (23.3 mmol) of tetrakis(triphenylphosphine)palladium(0), 3.7 L oftoluene and 1.74 L of aqueous solution of 2M sodium carbonate were addedtogether, and stirred at 90 degrees C. for 24 hours. After the reactionwas over, the mixture experienced filtration, through which aqueousphase thereof was eliminated. The organic phase thereof was washed bywater and dried with magnesium sulfate, and the toluene was thendistilled away under reduced pressure. Residue thereof was refined bysilica-gel column chromatography, such that 268 g of 1-(4-bromophenyl)naphthalene was obtained at an yield of 81%.

[Synthesis Reference 4-2] Synthesis of 4-(1-naphthyl)phenylboronic acid

Under an argon gas atmosphere, a mixture of 208.8 g (737.4 mmol) of1-(4-bromophenyl)naphthalene and 2.1 L of dehydrated TI-IF was cooleddown to minus 60 degree C. Then, 567 ml (884.9 mmol) of hexane solutionof 1.56M n-butyllithium was dropped into the mixture while the mixturewas being stirred. The reaction mixture was further stirred at minus 60degrees for 2 hours. 416 g (2.21 mol) of triisopropylborate was droppedinto the reaction mixture at minus 60 degrees C. The reaction mixturewas then stirred at room temperature for 17 hours. The reaction mixturewas added with aqueous solution of hydrochloric acid and stirred at roomtemperature for 1 hour. After the reaction, the reaction mixture wasadded with toluene, and aqueous phase thereof was eliminated. Then,organic phase thereof was dried with magnesium sulfate, and the solventwas distilled away under reduced pressure. By recrystallizing theobtained solid by toluene, 126 g of 4-(1-naphthyl)phenylboronic acid wasobtained at an yield of 67%.

[Synthesis Reference 5-1] Synthesis of 2-bromo-6-phenylnaphthalene

Under an argon gas atmosphere, 128.0 g (1.049 mol) of phenylboronicacid, 300.0 g (1.163 mol) of 2,6-dibromonaphthalene, 24.2 g (21.0 mmol)of tetrakis(triphenylphosphine)palladium(0), 4.3 L of dimethoxyethaneand 1.60 L of aqueous solution of 2M sodium carbonate were addedtogether, and stirred at 78 degrees C. for 24 hours. The reactionmixture was added with toluene and water, and aqueous phase thereof waseliminated. After organic phase thereof was washed by water and driedwith magnesium sulfate, the toluene was distilled away under reducedpressure. Residue thereof was refined by silica-gel columnchromatography and recrystallized with hexane such that 108 g of2-bromo-6-phenylnaphthalene was obtained at an yield of 36%.

[Synthesis Reference 5-2] Synthesis of 6-phenylnaphthalene-2-boronicacid

Under an argon gas atmosphere, a mixture of 100.0 g (353.1 mmol) of2-bromo-6-phenylnaphthalene, 1.2 L of dehydrated THF and 1.2 L ofdehydrated diethyl ether was cooled down to minus 20 degree C. Then, 280ml (437 mmol) of hexane solution of 1.56M n-butyllithium was droppedinto the mixture while the mixture was being stirred. The reactionmixture was further stirred at minus 20 degrees for 1 hour. The reactionmixture was cooled down to minus 60 degrees C., and 199.3 g (1.06 mol)of triisopropylborate was dropped into the mixture. The reaction mixturewas warmed up and then stirred at room temperature for 16 hours. Thereaction mixture was added with aqueous solution of hydrochloric acidand stirred at room temperature for 1 hour. After the reaction, thereaction mixture was added with toluene, and aqueous phase thereof waseliminated. Then, organic phase thereof was washed with water and driedwith magnesium sulfate, and the solvent was distilled away under reducedpressure. By recrystallizing the obtained solid with hexane, 58.0 g of6-phenylnaphthalene-2-boronic acid was obtained at an yield of 55%.

[Synthesis Reference 6-1] Synthesis of 2-(4-ethynylphenyl)naphthalene

Under an argon gas atmosphere, a mixture of 20.0 g (70.63 mmol) of2-(4-bromophenyl)naphthalene, 1.73 g (1.41 mmol) of PdCl₂(PPh₃)₂, 0.54 g(2.83 mmol) of CuI and 100 mL of triethylamine was cooled down to 0degree C., and added with 8.32 g (84.8 mmol) of trimethylsilylacetylene.Then, the mixture was stirred at room temperature for 4 hours. After thereaction was over, insoluble matters were removed by filtration, and thesolvent was distilled away. The obtained residue was added with aqueoussolution of hydrochloric acid, and extracted with toluene. After liquidseparation, organic phase thereof was washed with aqueous solution ofsodium hydrogencarbonate, and subsequently washed with water andsaturated sodium chloride solution. The organic phase was dried withanhydrous sodium sulfate. After filtration, the solvent was distilledaway. Then, the residue was refined by column chromatography, so that14.5 g of trimethyl((4-naphthalene-2-yl)phenyl)ethynyl)silane wasobtained at an yield of 68%.

A mixture of 14.5 g (48.3 mmol) of the obtainedtrimethyl((4-naphthalene-2-yl)phenyl)ethynyl)silane, tetrahydrofuran(THF) and methanol (MeOH) was added with 48 ml of 0.1M potassiumhydrate, and stirred at room temperature for 1 hour. The reactionmixture was added with water, and extracted with toluene. Organic phasethereof was washed with saturated sodium chloride solution and driedwith anhydrous sodium sulfate. After filtration, the solvent wasdistilled away. Residue thereof was refined by column chromatography,such that 9.5 g of 2-(4-ethynylphenyl)naphthalene was obtained at anyield of 86%.

[Synthesis Reference 7-1] Synthesis of 1-(4-ethynylphenyl)naphthalene

Under an argon gas atmosphere, a mixture of 20.0 g (70.63 mmol) of1-(4-bromophenyl)naphthalene, 1.73 g (1.41 mmol) of PdCl₂(PPh₃)₂, 0.54 g(2.83 mmol) of CuI and 100 mL of triethylamine was cooled down to 0degree C., and added with 8.32 g (84.8 mmol) of trimethylsilylacetylene.Then, the mixture was stirred at room temperature for 4 hours. After thereaction was over, insoluble matters were removed by filtration, and thesolvent was distilled away. The obtained residue was added with aqueoussolution of hydrochloric acid, and extracted with toluene. After liquidseparation, organic phase thereof was washed with aqueous solution ofsodium hydrogencarbonate, and subsequently washed with water andsaturated sodium chloride solution. The organic phase was dried withanhydrous sodium sulfate. After filtration, the solvent was distilledaway. Then, the residue was refined by column chromatography, so that15.2 g of trimethyl((4-naphthalene-1-yl)phenyl)ethynyl)silane wasobtained at an yield of 72%.

A mixture of 15.2 g (50.6 mmol) of the obtainedtrimethyl((4-naphthalene-1-yl)phenyl)ethynyl)silane, THF and MeOH wasadded with 48 ml of 0.1M potassium hydrate, and stirred at roomtemperature for 1 hour. The reaction mixture was added with water, andextracted with toluene. Organic phase thereof was washed with saturatedsodium chloride solution and dried with anhydrous sodium sulfate. Afterfiltration, the solvent was distilled away. Residue thereof was refinedby column chromatography, such that 9.8 g of1-(4-ethynylphenyl)naphthalene was obtained at an yield of 85%.

[Synthesis Reference 8-1] Synthesis of 2-(3-ethynylphenyl)naphthalene

Under an argon gas atmosphere, a mixture of 25.0 g (88.3 mmol) of2-(3-bromophenyl)naphthalene, 2.17 g (1.77 mmol) of PdCl₂(PPh₃)₂, 0.67 g(3.53 mmol) of CuI and 120 mL of triethylamine was cooled down to 0degree C., and added with 10.41 g (106 mmol) of trimethylsilylacetylene.Then, the mixture was stirred at room temperature for 4 hours. After thereaction was over, insoluble matters were removed by filtration, and thesolvent was distilled away. The obtained residue was added with aqueoussolution of hydrochloric acid, and extracted with toluene. After liquidseparation, organic phase thereof was washed with aqueous solution ofsodium hydrogencarbonate, and subsequently washed with water andsaturated sodium chloride solution. The organic phase was dried withanhydrous sodium sulfate. After filtration, the solvent was distilledaway. Then, the residue was refined by column chromatography, so that19.0 g of trimethyl((3-naphthalene-2-yl)phenyl)ethynyl)silane wasobtained at an yield of 72%.

A mixture of 19.0 g (63.2 mmol) of the obtainedtrimethyl((3-naphthalene-2-yl)phenyl)silane, THF and MeOH was added with60 mL of aqueous solution of 0.1M potassium hydrate, and stirred at roomtemperature for 1 hour. The reaction mixture was added with water, andextracted with toluene. Organic phase thereof was washed with saturatedsodium chloride solution and dried with anhydrous sodium sulfate. Afterfiltration, the solvent was distilled away. Residue thereof was refinedby column chromatography, such that 12.5 g of2-(3-ethynylphenyl)naphthalene was obtained at an yield of 87%.

Synthesis Example 1-1 Synthesis of Compound 1-1

Under an argon gas atmosphere, 10.0 g (29.8 mmol) of2,7-dibromophenanthrene, 7.38 g (29.8 mmol) of3-(1-naphthyl)phenylboronic acid, 0.69 g (0.60 mmol) of tetrakis(triphenylphosphine) palladium(0), 200 mL of toluene, 50 mL ofdimethoxyethane and 44.6 mL of aqueous solution of 2M sodium carbonatewere mixed, and stirred at 90 degrees C. for 10 hours. Subsequently, thereaction mixture was cooled down to room temperature, added with waterand stirred for one hour. Then, the reaction mixture was extracted withtoluene. After liquid separation, organic phase thereof was washed withsaturated sodium chloride solution and dried with anhydrous sodiumsulfate. The solvent was distilled away under reduced pressure, and theresidue was refined by silica-gel column chromatography andrecrystallized by toluene, such that 3.93 g of2-bromo-7-(3-(naphthalene-1-yl)phenyl)phenanthrene was obtained at anyield of 29%.

Under an argon gas atmosphere, 3.93 g (8.56 mmol) of2-bromo-7-(3-(naphthalene-1-yl)phenyl)phenanthrene, 1.54 g (8.98 mmol)of 2-naphthaleneboronic acid, 0.20 g (0.17 mmol) oftetrakis(triphenylphosphine) palladium(0), 100 mL of toluene and 12.8 mLof aqueous solution of 2M sodium carbonate were mixed, and stirred at 90degrees C. for 10 hours. Subsequently, the reaction mixture was cooleddown to room temperature, added with water and stirred for 1 hour atroom temperature. After the solid was separated by filtration, theobtained solid was washed with water, methanol, dimethoxyethane andtoluene in this order. The obtained solid was thermally melted intoluene, refined by silica-gel column chromatography and furtherrecrystallized with toluene. Then, 2.60 g of the compound 1-1 wasobtained at an yield of 60%.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-2 Synthesis of Compound 1-2

The compound 1-2 was synthesized in the same manner as the compound 1-1,except that 3-(2-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid and that 1-naphthaleneboronic acid wasused in place of 2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-3 Synthesis of Compound 1-5

The compound 1-5 was synthesized in the same manner as the compound 1-1,except that 3-(2-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-4 Synthesis of Compound 1-6

The compound 1-6 was synthesized in the same manner as the compound 1-1,except that 4-(1-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid and that 1-naphthaleneboronic acid wasused in place of 2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-5 Synthesis of Compound 1-8

The compound 1-8 was synthesized in the same manner as the compound 1-1,except that 2-naphthaleneboronic acid was used in place of3-(1-naphthyl)phenylboronic acid and that 4-biphenylboronic acid wasused in place of 2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 456while a calculated molecular weight was 456.2.

Synthesis Example 1-6 Synthesis of Compound 1-9

The compound 1-9 was synthesized in the same manner as the compound 1-1,except that 4-(1-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-7 Synthesis of Compound 1-13

The compound 1-13 was synthesized in the same manner as the compound1-1, except that 4-(2-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-8 Synthesis of Compound 1-17

The compound 1-17 was synthesized in the same manner as the compound1-1, except that 1-naphthaleneboronic acid was used in place of2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-9 Synthesis of Compound 1-18

The compound 1-18 was synthesized in the same manner as the compound1-1, except that 3-(2-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid and that 6-phenyl-2-naphthaleneboronicacid was used in place of 2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 582while a calculated molecular weight was 582.23.

Synthesis Example 1-10 Synthesis of Compound 1-21

The compound 1-21 was synthesized in the same manner as the compound1-1, except that 4-(2-naphthyl)phenylboronic acid was used in place of3-(1-naphthyl)phenylboronic acid and that 1-naphthaleneboronic acid wasused in place of 2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 506while a calculated molecular weight was 506.2.

Synthesis Example 1-11 Synthesis of Compound 1-61

Under an argon gas atmosphere, a mixture of 10.0 g (32.3 mmol) of2-bromo-o-terphenyl, 8.12 g (35.6 mmol) of2-(4-ethynylphenyl)naphthalene and 120 mL of triethylamine was addedwith 0.79 g (0.65 mmol) of PdCl₂(PPh₃)₂ and 0.25 g (1.29 mmol) of CuI.Then, the mixture was stirred at 60 degrees C. for 4 hours. After thereaction was over, insoluble matters were removed by filtration, and thesolvent was distilled away under reduced pressure. The reaction mixturewas added with aqueous solution of hydrochloric acid, and extracted withtoluene. Organic phase thereof was washed with aqueous solution ofsodium hydrogencarbonate, and subsequently washed with water andsaturated sodium chloride solution. After liquid separation, the organicphase was dried with anhydrous sodium sulfate and followed byfiltration. The solvent was then distilled away. The residue was refinedby column chromatography, so that 7.8 g of2-(4-(terphenyl-2-ylethynyl)phenyl)naphthalene was obtained at an yieldof 83%.

Under an argon gas atmosphere, a mixture of 5.00 g (11.0 mmol) of2-(4-(terphenyl-2-ylethynyl)phenyl)naphthalene and 85 mL ofdichloromethane was cooled down to minus 78 degree C., and added with amixture containing 2.13 g (13.1 mmol) of IC1 and 30 mL ofdichloromethane. The mixture was stirred at minus 78 degrees C. for 1hour.

The reaction mixture was added with aqueous solution of sodiumbisulfite, and extracted with dichloromethane. The organic phase waswashed with water and saturated sodium chloride solution. The organicphase was dried with anhydrous sodium sulfate. After filtration, thesolvent was distilled away. Then, the residue was refined by flashcolumn chromatography, so that 4.6 g of9-iodo-10-(4-(naphthalene-2-yl)phenyl)-4-phenylphenanthrene was obtainedat an yield of 72%.

Under an argon gas atmosphere, a mixture of 3.0 g (5.15 mmol) of1,4-bis(10-iodo-7-phenylphenanthrene-9-yl)benzene and 60 mL ofdehydrated THF was cooled down to minus 70 degree C. Then, 7.73 ml (7.73mmol) of hexane solution of 1.00M s-butyllithium was dropped into themixture while the mixture was being stirred. The mixture was stirred atminus 70 degrees C. for 30 minutes. The reaction mixture was added with30 mL of MeOH, warmed up to room temperature and stirred for 1 hour. Thereaction mixture was added with aqueous solution of hydrochloric acid,and extracted with toluene. The organic phase was washed with water andsaturated sodium chloride solution. The organic phase was dried withanhydrous sodium sulfate. After filtration, the solvent was distilledaway. Then, the residue was refined by flash column chromatography, sothat 1.32 g of the compound 1-61 was obtained at an yield of 56%.

Mass-spectrum analysis consequently showed that m/e was equal to 456while a calculated molecular weight was 456.19.

Synthesis Example 1-12 Synthesis of Compound 1-76

The compound 1-76 was synthesized in the same manner as the compound1-61, except that 2-bromo-p-terphenyl was used in place of2-bromo-o-terphenyl and that 1-naphthaleneboronic acid was used in placeof 2-naphthaleneboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 456while a calculated molecular weight was 456.19.

Synthesis Example 1-13 Synthesis of Compound 1-77

The compound 1-77 was synthesized in the same manner as the compound1-61, except that 2-bromo-p-terphenyl was used in place of2-bromo-o-terphenyl and that 1-(4-ethynylphenyl)naphthalene was used inplace of 2-(4-ethynylphenyl)naphthalene.

Mass-spectrum analysis consequently showed that m/e was equal to 456while a calculated molecular weight was 456.19.

Synthesis Example 1-14 Synthesis of Compound 1-78

The compound 1-78 was synthesized in the same manner as the compound1-61, except that 2-bromo-p-terphenyl was used in place of2-bromo-o-terphenyl and that 2-(3-ethynylphenyl)naphthalene was used inplace of 2-(4-ethynylphenyl)naphthalene.

Mass-spectrum analysis consequently showed that m/e was equal to 456while a calculated molecular weight was 456.19.

Synthesis Example 1-15 Synthesis of Compound 1-91

Under an argon gas atmosphere, a mixture of 10.0 g (32.3 mmol) of2-bromo-p-terphenyl, 3.63 g (35.6 mmol) of ethynylbenzene and 90 mL oftriethylamine was added with 0.79 g (0.65 mmol) of PdCl₂(PPh₃)₂ and 0.25g (1.29 mmol) of CuI. Then, the mixture was stirred at 60 degrees C. for4 hours. After the reaction was over, insoluble matters were removed byfiltration, and the solvent was distilled away under reduced pressure.The reaction mixture was added with aqueous solution of hydrochloricacid, and extracted with toluene. Organic phase thereof was washed withaqueous solution of sodium hydrogencarbonate, and subsequently washedwith water and saturated sodium chloride solution. After liquidseparation, the organic phase was dried with anhydrous sodium sulfateand followed by filtration. The solvent was then distilled away. Theresidue was refined by column chromatography, so that 7.4 g of2′-(phenylethynyl)biphenyl-4-ylbenzene was obtained at an yield of 69%.

Under an argon gas atmosphere, a mixture of 7.4 g (22.4 mmol) of2′-(phenylethynyl)biphenyl-4-ylbenzene and 140 mL of dichloromethane wascooled down to minus 78 degree C., and added with a mixture containing4.36 g (26.9 mmol) of IC1 and 60 mL of dichloromethane. The mixture wasstirred at minus 78 degrees C. for 1 hour.

The reaction mixture was added with aqueous solution of sodiumbisulfite, and extracted with dichloromethane. The organic phase waswashed with water and saturated sodium chloride solution. The organicphase was dried with anhydrous sodium sulfate. After filtration, thesolvent was distilled away. Then, the residue was refined by flashcolumn chromatography, so that 7.3 g of 9-iodo-2,10-diphenylphenanthrenewas obtained at an yield of 71%.

Under an argon gas atmosphere, 3.00 g (6.57 mmol) of9-iodo-2,10-diphenylphenanthrene, 1.79 g (7.23 mmol) of4-(2-naphthyl)phenylboronic acid, 0.38 g (0.33 mmol) oftetrakis(triphenylphosphine) palladium(0), 30 mL of toluene, 30 mL ofdimethoxyethane and 9.86 g (19.7 mmol) of aqueous solution of 2M sodiumcarbonate were mixed, and stirred at 80 degrees C. for 10 hours.Subsequently, the reaction mixture was cooled down to room temperature,added with water and stirred for 1 hour at room temperature. After thesolid was separated by filtration, the obtained solid was washed withwater, methanol, dimethoxyethane and toluene in this order. The obtainedsolid was thermally melted in toluene, refined by silica-gel columnchromatography and further recrystallized with toluene. Then, 2.10 g ofthe compound 1-91 was obtained at an yield of 60%.

Mass-spectrum analysis consequently showed that m/e was equal to 532while a calculated molecular weight was 532.22.

Synthesis Example 1-16 Synthesis of Compound 1-93

The compound 1-93 was synthesized in the same manner as the compound1-91, except that 3-(2-naphthyl)phenylboronic acid was used in place of4-(2-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 532while a calculated molecular weight was 532.22.

Synthesis Example 1-17 Synthesis of Compound 1-111

The compound 1-111 was synthesized in the same manner as the compound1-91, except that 2-bromobiphenyl was used in place of2-bromo-p-terphenyl and that 2-(4-ethynylphenyl)naphthalene was used inplace of ethynylbenzene.

Mass-spectrum analysis consequently showed that m/e was equal to 582while a calculated molecular weight was 582.23.

Synthesis Example 1-18 Synthesis of Compound 1-112

The compound 1-112 was synthesized in the same manner as the compound1-91, except that 2-bromobiphenyl was used in place of2-bromo-p-terphenyl, that 2-(3-ethynylphenyl)naphthalene was used inplace of ethynylbenzene and that 3-(2-naphthyl)phenylboronic acid wasused in place of 4-(2-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 582while a calculated molecular weight was 582.23.

Synthesis Example 1-19 Synthesis of Compound 1-113

The compound 1-113 was synthesized in the same manner as the compound1-91, except that 2-bromobiphenyl was used in place of2-bromo-p-terphenyl, that 1-(4-ethynylphenyl)naphthalene was used inplace of ethynylbenzene and that 4-(1-naphthyl)phenylboronic acid wasused in place of 4-(2-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 582while a calculated molecular weight was 582.23.

Synthesis Example 1-20 Synthesis of Compound 1-114

The compound 1-114 was synthesized in the same manner as the compound1-91, except that 2-bromobiphenyl was used in place of2-bromo-p-terphenyl, that 1-(3-ethynylphenyl)naphthalene was used inplace of ethynylbenzene and that 3-(1-naphthyl)phenylboronic acid wasused in place of 4-(2-naphthyl)phenylboronic acid.

Mass-spectrum analysis consequently showed that m/e was equal to 582while a calculated molecular weight was 582.23.

An equipment used in the measurement of mass spectrometry andmeasurement conditions thereof in the above synthesis examples will bedescribed below.

-   -   Equipment: JSM-700 (manufactured by Japan Electron Optics        Laboratories Ltd.)    -   Condition: accelerating voltage 8 kV        -   scanning range m/z=50 to 3000    -   Emitter type: carbon    -   Emitter currency: 0 mA→2 mA/minute→40 mA (maintained for 10        minutes)

EXAMPLES

Next, the invention will be described in further detail with referenceto examples. However, the invention is not limited to such examples.

Structures of compounds used in Examples and Comparatives will be shownbelow.

Example 1 Manufacturing of Organic EL Device

A glass substrate (size: 25 mm×75 mm×0.7 mm thick) having an ITOtransparent electrode (manufactured by Asahi Glass Co., Ltd) wasultrasonic-cleaned in isopropyl alcohol for five minutes, and thenUV/ozone-cleaned for 30 minutes. After the glass substrate having thetransparent electrode line was cleaned, the glass substrate was mountedon a substrate holder of a vacuum deposition apparatus, so that 50-nmthick film of HT1 was initially formed on a surface of the glasssubstrate where the transparent electrode line was provided so as tocover the transparent electrode. The HT1 film serves as a holeinjecting/transporting layer. Subsequently to the formation of the holeinjecting/transporting layer, 40-nm thick film of the new host compound1-1 and Ir(piq)₃ as a phosphorescent-emitting dopant were co-depositedby resistance heating so that Ir(piq)₃ was contained therein at acontent of 10 mass %. The co-deposited film serves as an emitting layer(phosphorescent-emitting layer). After the film of the emitting layerwas formed, 40-nm thick film of ET1 was formed. The film of ET1 servesas an electron transporting layer. Then, 0.5-nm thick film of LiF wasformed as an electron-injecting electrode (cathode) at a film-formingspeed of 1 Å/min. Metal (Al) was vapor-deposited on the LiF film to forma 150-nm thick metal cathode, thereby providing the organic EL device.

Examples 2 to 20 and Comparatives 1 to 3

The organic EL devices according respectively to Examples 2 to 20 andComparatives 1 to 3 were formed in the same manner as Example 1 exceptthat host compounds shown in Table 1 were respectively used in place ofthe new host compound 1-1.

[Evaluation on Emitting Performance of Organic EL Device]

The organic EL devices according to Examples 1 to 20 and Comparatives 1to 3 each were driven by direct-current electricity to emit light, sothat voltage, luminous efficiency and time elapsed until the initialluminance intensity of 3000 cd/m² was reduced to the half (i.e., timeuntil half-life) at a current density of 10 mA/cm² were measured foreach organic EL device. Then, pixel uniformity when each organic ELdevice was driven at 70 degrees C. was visually checked, among whichdevices having uniform pixels are rated as A while devices havingnon-uniform pixels are rated as B. The results of the evaluation areshown in Table 1.

TABLE 1 Luminous Time until Pixel Uniformity Host Voltage EfficiencyHalf-Life when Driven Example Compound (V) (cd/A) (hour) at 70 C. °Example 1 1-1  5.4 8.4 8000 A Example 2 1-2  5.2 7.9 9000 A Example 31-5  5.3 8.2 8500 A Example 4 1-6  5.5 10.3 7000 A Example 5 1-8  5.17.8 8000 A Example 6 1-9  5.4 9.2 7000 A Example 7 1-13 5.2 8.5 8000 AExample 8 1-17 5.5 10.1 7500 A Example 9 1-18 5.3 8.0 9000 A Example 101-21 5.2 7.5 10000 A Example 11 1-61 5.5 9.8 12000 A Example 12 1-76 5.49.5 12000 A Example 13 1-77 5.3 9.4 11000 A Example 14 1-78 5.4 9.313000 A Example 15 1-91 5.4 9.5 10000 A Example 16 1-93 5.5 9.5 11000 AExample 17  1-111 5.6 9.6 9000 A Example 18  1-112 5.6 9.6 9000 AExample 19  1-113 5.5 9.5 9000 A Example 20  1-114 5.5 9.4 9500 AComparative 1 CBP 5.4 6.3 1200 B Comparative 2 Compound A 5.5 7.2 800 BComparative 3 Compound B 5.4 6.5 1100 B

As appreciated from the above, in comparison with Comparatives 1 to 3,the organic EL devices according to Examples 1 to 20, in which thephenanthrene derivative according to the aspect of the invention wasused as the host of the phosphorescent-emitting layer, were excellent interms of the time until half-life, pixel uniformity when driven at ashigh a temperature as 70 degrees C. and luminous efficiency.

Accordingly, the organic EL device according to the aspect of theinvention are excellent in luminous efficiency, heat resistance andlifetime and free from pixel defects.

INDUSTRIAL APPLICABILITY

The invention is applicable to a phenanthrene derivative, a material fororganic EL devices and an organic EL device using the same.

1. A phenanthrene derivative, represented by a formula (I) below,

where: Ar¹ and Ar² each represent an aromatic hydrocarbon ring grouphaving 6 to 18 carbon atoms for forming the ring, the aromatichydrocarbon ring group containing none of anthracene skeleton, pyreneskeleton, aceanthrylene skeleton and naphthacene skeleton, optionally,Ar¹ and Ar² being bonded in any positions of a phenanthrene skeleton; R¹represents an alkyl group, cycloalkyl group, alkoxy group, cyano group,silyl group, halogen atom or aryl group, optionally, R¹ being be bondedin any position of the phenanthrene skeleton; k represents an integer of0 to 8, k representing the number of substituents R¹ directly bonded toa phenanthrene main chain, optionally, the plurality of R¹ beingmutually the same or different when k is 2 or more; n and m eachrepresent an integer of 1 to 3, optionally, the pluralities of Ar¹ andAr² being independently the same or different when m+n≧2; and when(—[Ar¹]_(m)—H)=(—[Ar²]_(n)—H), either one of (—[Ar¹]_(m)—H) and(—[Ar²]_(n)—H) is bonded in 1st, 4th, 5th, 8th, 9th or 10th position ofthe phenanthrene skeleton.
 2. The phenanthrene derivative according toclaim 1, wherein Ar¹ and Ar² in the formula (1) represent a groupselected from the group consisting of a substituted or unsubstitutedbenzene skeleton, naphthalene skeleton, fluorene skeleton, fluorantheneskeleton, triphenylene skeleton, chrysene skeleton, benzophenanthreneskeleton, dibenzophenanthrene skeleton, benzotriphenylene skeleton,picene skeleton and benzo[b]fluoranthene skeleton.
 3. The phenanthrenederivative according to claim 1, wherein k is 0, 1 or
 2. 4. Thephenanthrene derivative according to claim 1, wherein when Ar¹ and Ar²in the formula (1) have substituent(s), the substituent(s) is a groupselected from the group consisting of an alkyl group, cycloalkyl group,alkoxy group, cyano group, silyl group and halogen atom.
 5. Thephenanthrene derivative according to claim 1, wherein (—[Ar¹]_(m)—H) isnot equal to (—[Ar²]_(n)—H) in the formula (1).
 6. The phenanthrenederivative according to claim 1, wherein the formula (1) is representedby any one of formulae (1-a) to (1-l) below.


7. A material for an organic EL device, comprising the phenanthrenederivative according to claim
 1. 8. The material for an organic ELdevice devices according to claim 7, wherein the EL device comprises aphosphorescent-emitting material.
 9. The material for organic EL devicesaccording to claim 7, wherein the material is a host material of anemitting layer.